Volume Contents 1997 NUMBER 1 Contents Tetrahedron Prize for Creativity in Organic Chemistry Contributors to this Issue Graphical Abstracts Dariel P. Becker, Roger Nosal, Synthetic strategies for the construction of enantiomeric azanoradamantanes Daniel L. Zabrowski and Daniel L. Flynn Raymond C. Harden, Lewis acid-catalysed rearrangement/reduction of 1-phenyloxiranemeth- Timothy J. Hodgkinson, anamines: synthesis of B-phenethylamines Alexander McKillop, Will G. Prowse and Michaei W. J. Urquhart Gary H. Posner, Liuisa Gonzalez, Synthesis and antimalarial activity of heteroatom-containing bicyclic Jared N. Cumming, endoperoxides Donna Klinedinst and Theresa A. Shapiro Masatomo Iwao and A concise total synthesis of (+)-cis- and (+)-trans-clavicipitic acids by Fumito Ishibashi combinational use of directed lithiation and fiuoride ion-induced elimination— addition reaction of 1-(triisopropylsilyl)gramine derivatives Cheng-Bin Cui, Hideaki Kakeya and Novel mammalian cell cycle inhibitors, cyclotryprostatins A—-D, produced by Hiroyuki Osada Aspergillus fumigatus, which inhibit mammalian cell cycle at G2/M phase ——— Kim, Kwang Sub Yoon Kinetic studies of intramolecular additions of alkyl radicals onto imines and Yong Suk Kim T. Troll, H. Beckel and Electrochemical synthesis of substituted indolizines; UV and fluorescence C. Lentner-Béhm spectra Hans-Joachim Kndlker, Enantioselective synthesis of calcitriol A-ring fragments Achim Ecker, Petra Struwe, Andreas Steinmeyer, Gunnar Miller and Ginter Neef Walter Werner, Udo Grafe, Synthesis of tolypocladin and isotolypociadin Wolfgang Ihn, Dieter Tresselit, Stefan Winter and Erich Paulus ingo Schlachter, Jochen Mattay, Combined quantum chemical and MM-approach to the endo/exo selectivity Josef Suer, Udo Héweler, of Diels—Alder reactions in polar media Gudrun Wirthwein and Ernst-Uirich Warthwein 188 Tetrahedron Christoph Schneider and Highly stereoselective Cope rearrangements of enantiomerically pure, Markus Rehfeuter silylated syn-aldols Jacques Lebreton, Chemoenzymatic synthesis of marine brown algae pheromones Véronique Alphand and Roland Furstoss Ahmad M. Farag, Kamal M. Dawood Facile synthesis of novel polysubstituted thiophene and 1,3,4-thiadiazole and Zaghioul E. Kandeel derivatives Maria Antonietta Casadei, The O,*/CO, system as mild and safe carboxylating reagent synthesis of Stefania Cesa, Marta Feroci, organic carbonates Achille inesi, Leucio Rossi and Franco Micheletti Moracci Tatyana |. Mukhanova, B-(Benzofur-2-yl)- and (indol-2-yl)enamines in the Nenitzescu reaction Elena K. Panisheva, Valeriya M. Lyubchanskaya, Lyudmila M. Alekseeva, Yuryi N. Sheinker and Viadimir G. Granik Hans-Jirgen Hamann, Eugen Hoft, New optically pure sugar hydroperoxides. Synthesis and use for enantio- Danuta Mostowicz, selective oxygen transfer Anatoly Mishnev, Zofia Urbariczyk-Lipkowska and Marek Chmielewski Mieczystaw Makosza, Synthesis of a 1,3,4,5-tetrahydrobenz[cojindole via the vicarious nucleophilic Jacek Stalewski, substitution of hydrogen Krzysztof Wojciechowski and Witold Danikiewicz Gudmundur G. Haraldsson and A selective cleavage of aromatic benzyl ethers located ortho to a carbonyl Jack E. Baldwin group by magnesium bromide Takatoshi Matsumoto, Theoretical study of the reaction of silyiketenes with acyl isocyanates Kiyo Takaoka, Toyohiko Aoyama and Takayuki Shioiri Mikael Jonassohn, Ralf Davidsson, The reactivity of drimane unsaturated dialdehydes towards nucleophiles Pia Kahnberg and Olov Sterner Richard H. Furneaux, The chemistry of castanospermine—V. Synthetic modifications at C-1 and C- Graeme J. Gainsford, 7 Jennifer M. Mason, Peter C. Tyler, Oliver Hartley and Bryan G. Winchester Ana M. Rosa, Ana M. Lobo, Synthesis of phenanthridines by radical C,,,-C,,,, coupling Paula S. Branco, Sundaresan Prabhakar and Antonio M. D. L. Pereira Ana M. Rosa, Ana M. Lobo, The chemistry and reactivity of aryl radicals—the C—C bond formation from Paula S. Branco and o-bromobenzyiphenylethers with tin hydride and azobisisobutyronitrile Sundaresan Prabhakar Ana M. Rosa, Ana M. Lobo, New syntheses of the Amaryilidacaea alkaloids vasconine, assoanine, Paula S. Branco, oxoassoanine, pratosine and ismine by radical cyclisation Sundaresan Prabhakar and Margarida Sa-da-Costa Eifion D. Phillips, E. Sarah Warren Alkene synthesis from allylic sulfones: preparation of isopropenyl and and Gordon H. Whitham isopropylidene isomers from a common intermediate Bhanudas P. Kavitake, Binding of oligonucleotides by use of nonnucleotide linkers Suchita V. Patil and Manikrao M. Salunkhe Maria J. Ortega, Eva Zubia, New cytotoxic metabolites from the sponge Mycale micracanthoxea J. Luis Carballo and Javier Saliva Wadi Ajana, Synthesis of pyrido[2,3-bjacridine-5,11,12-triones Francisco Lépez-Calahorra, John A. Joule and Mercedes Alvarez Marco C. Cleij, Fabrizio Mancin, Chiral lipophilic ligands—V. Enantioselective ester cleavage of a-amino Paolo Scrimin, Paolo Tecilia and esters by Cu(II) complexes of chiral diamino alcohols in aqueous surfactants Umberto Tonellato solutions Tetrahedron 189 Mikael Elofsson, Preparation of Tn and sialyl Tn building blocks used in Fmoc solid-phase Lourdes A. Salvador and synthesis of glycopeptide fragments from HIV gp120 Jan Kihlberg Miroslav Otmar, Reductive cyclization of 6-cyanomethyl-5-nitropyrimidines—an efficient route Milena Masojidkova and to 7-alkyl-5H-pyrrolo[3,2-d]pyrimidines and 6-amino-7 ,7-dialkyl-7 H-pyrrolo- Antonin Holy [3,2-d)pyrimidines. Utilization in the synthesis of 9-deaza analogues of DHPA Instructions to Contributors NUMBER 2 Contents Contributors to this Issue Graphical Abstracts Corrigenda TETRAHEDRON REPORT NUMBER 411 Martyn Frederickson Optically active isoxazolidines via asymmetric cycloaddition reactions of nitrones with alkenes: applications in organic synthesis ARTICLES Raymond J. Bergeron, MeiGuo Xin, Total synthesis of rhizoferrin, an iron chelator Richard E. Smith, Markus Wollenweber, James S. McManis, Christian Ludin and Khalil A. Abboud Carolina Cerré, Alan F. Hofmann, Oxyfunctionalization of (5B)-bile acids by dimethyidioxirane: hydroxylation at Claudio D. Schteingart, Weiping Jia C-5, C-14, and C-17 and David Maltby Morris J. Robins, Sanchita Sarker, Nucleic acid related compounds—XCIV. Remarkably high stereoselective Vicente Samano and reductions of 2'- and 3'-ketonucleoside derivatives to give arabino, ribo, and Stanislaw F. Wnuk xylofuranosyl nucleosides with hydrogen isotopes at C2' and C3' Mark R. DeLuca and Sean M. Kerwin The para-toluenesulfonic acid-promoted synthesis of 2-substituted benzoxazoles and benzimidazoles from diacylated precursors Norbert M. Maier and Dynamic equilibration of diastereomeric salts of atropisomers. Proton NMR John A. Zoltewicz spectra of 1,8-di(3'-pyridyl)naphthalene in the presence of A-camphorsulfonic acid Bernardo A. Frontana, Preparative electrochemical reductive methylation of ortho-hydroxy-para- —_ Cardenas, benzoquinones Lydia Rodriguez-Hahn and Alejandro Baeza R. Alan Jones, Joachim Pastor, Pyrroloindole analogues of ellipticine. The synthesis and DNA intercalative Jorge Siro and Tevita N. Voro properties of 5,10-dihydro-5, 10-dimethyl-2,5, 10-triazadibenzo/a,e]pentalene Derek H. R. Barton and The selective functionalization of saturated hydrocarbons—XXXVII. Béatrice M. Chabot Utilization of a new oxidant: bis(trimethylsilyl) peroxide Derek H. R. Barton and The selective functionalization of saturated hydrocarbons—XXXVIII. Bis(tri- Béatrice M. Chabot methylsilyl) peroxide: an efficient oxidant for the functionalization of hydrocarbons involving the Fe'—Fe'’ manifold Elen G. Juagdan, Raju Kalidindi and Two new chamigranes from an Hawaiian red alga, Laurencia cartilaginea Paul Scheuer 190 Tetrahedron Gloria L. Silva, Roberto R. Gil, 529 Novel cytotoxic ring-A seco-cycioartane triterpenes from Gardenia coronaria Baoliang Cul, Heebyung Chai, and G. Sootepensis Thawatchai Santisuk, Ekarath Srisook, Vichai Reutrakul, Patoomratana Tuchinda, Smaisukh Sophasan, Suparp Sujarit, Suchart Upatham, Sean M. Lynn, John E. Farthing, Shi-Lin Yang, Jane A. Lewis, Melanie J. O'Neill, Norman R. Farnsworth, Geoffrey A. Cordell, John M. Pezzuto and A. Douglas Kinghorn Yukitoshi Narukawa, Koichi Nishi General and efficient synthesis of 2-alkyicarbapenems: synthesis of dethia- and Hiroshi Onouve carba analogs of clinically useful carbapenems via palladium-catalyzed cross-coupling reaction Takeshi Takeda, Rika Sasaki, Transformation of ketones and aldehydes to gem-dihalides via hydrazones Satoshi Yamauchi and using copper(!!) halides Tooru Fujiwara Kenichi Akaji, Yasunori Tamai and Efficient synthesis of peptaibol using a chloroimidazolidium coupling reagent Yoshiaki Kiso CIP Mitsuru Ohkubo, Synthesis of NB-506, a new anticancer agent Hiroshi Kawamoto, Toshiyuki Ohno, Masato Nakano and Hajime Morishima Satoshi Obika, Studies on novel and chiral 1,4-dihydropyridines—il!. Asymmetric reduction Toshihiko Nishiyama, of some ketones with novel NADH model compounds, (S,)-3-(p-tolyisulfiny!)- Satoshi Tatematsu, 1,4-dihydropyridines Kazuyuki Miyashita, Chuzo Iwata and Takeshi imanishi Yoshiji Takemoto, Satoru Kuraoka, Diastereoselective total synthesis of (—)-solavetivone via a copper-catalyzed Talichi Ohra, Yasuhiro Yonetoku conjugate addition of Me,Al to a cyclohexa-2,5-dienone intermediate and Chuzo Iwata Dean V. Johnson and The chemoenzymatic synthesis of (S)-13-hydroxyoctadeca-(9Z, 1 1 E)-dienoic Herfried Grieng! acid using the hydroxynitrile lyase from Hevea brasiliensis Ahmed H. Moustafa, 3,4-Dihydroquinolinium salts: preparation by reaction of N-aryinitrilium salts Martin G. Hitzier, Martin Lutz and with alkenes Johannes C. Jochims T. Masquelin and D. Obrecht A novel access to 2,4-substituted quinolines from acetylenic ketones Didier F. Andrés, Ulrike Dietrich, Anodic fiuorination of vinyl sulfides—synthesis of a-fluoro-B-thio-a,p- Eliane G. Laurent and unsaturated carbonyl compounds Bernard S. Marquet Kassoum Nacro, Michel Baltas, Stereoselective synthesis of five and/or six membered ring hydroxylactones Jean-Marc Escudier and obtained by Lewis acid mediated reaction of y,6-epoxy-B-hydroxyesters Liliane Gorrichon access to 5-methylated 2-deoxysugars Denyse Heriem and Chemistry of larixol—t!. Hemisynthesis of (—)-borjatriol Francoise Khuong-Huu Julio Delgado, Amparo Espinés, 2,4,6-Triphenyipyrylium tetrafluoroborate-photosensitized reactions of o-cinn- M. Consuelo Jiménez, amyiphenols and o-hydroxystilbenes Miguel A. Miranda and Rosa Tormos Viadimir Vinkovié and Vitomir Sunji¢ A highly stereocontrolied synthesis of (S)-(—)-3-(4-tert-butyl)phenyi-1-N-(cis- 2,6-dimethyl)morpholinyl-2-methyipropane via asymmetric Mannich reaction Anja Hansen, Tina M. Tagmose and Synthesis of the first 1-azaanalogues of L-sugars Mikael Boils Evdoxia Coutoull-Argyropoulou, Formation and reduction reactions of 3-indol-3-yl-isoxazolidines Elizabeth Malamidou-Xenikaki, Xenophon N. Stampelos and irini N. Alexopoulou Mercedes Amat, Nuria Lior, Preparation of enantiopure 6-(3-indolyl)-2-piperidones and conjugate Joan Bosch and Xavier Solans additions to a 3,4-didehydro derivative Tetrahedron 191 Carlo Dell’Erba, Angelo Mugnoli, Substituent effects on the gas-phase basicities of 4-X-acetophenones and 4- Renato Noto, Marino Novi, X-2,6-dimethylacetophenones: a comparison with solution basicities Giorgio Occhiucci, Giovanni Petrillo, Fernando Sancassan and Domenico Spinelli Dariusz Socha, Margarita Jurczak Synthesis of acosamirne and daunosamine from sugar 5-enelactones and Marek Chmielewski Elizabeth Malamidou-Xenikaki, A study on the reactions of indol-3-yl-carbaldehyde oximes with electrophilic Xenophon N. Stampelos, alkenes/alkynes. Generation of nitrones from the O-H oximes. 4n-Partici- Theodore A. Charalambis and pation of the O—Me oximes in Diels—Alder reactions Catherine C. Karapostoiou A. Rob P. M. Valentijn, Solid-phase synthesis of lysine-based cluster galactosides with high affinity Gijs A. van der Marel, for the asialoglycoprotein receptor Leo A. J. M. Sliedregt, Theo J. C. van Berkel, Erik A. L. Biessen and Jacques H. van Boom Anders Tsirk, Salo Gronowitz and Synthesis of substituted benzo[bjindolizidines and benzo[bjquinolizidines via Anna-Britta Hérnfeidt ring-opening of 3-bromo-2,5-dimethylthiophene-1 ,1 -dioxide Giuseppe Bellucci, Cinzia Chiappe, Concentration dependence of the steric course of bromine addition to Roberto Bianchini, Peter Lemmen acenaphthylene. A product and kinetic study and Dieter Lenoir Steven Coulton, Catalytic hydrogenation of N-tbutoxycarbonylindoles Thomas L. Gilchrist and Keith Graham Instructions to Contributors NUMBER 3 Contents Contributors to this Issue Graphical Abstracts Xiong Fu, Syed A. Abbas, New acetylenic metabolites from the marine sponge Pellina triangulata Francis J. Schmitz, lian Vidavsky, Michael L. Gross, Maureen Laney, Randal! C. Schatzman and Ronnei D. Cabusiay Tsutomu Yokomatsu, Facile synthesis of aryl(difiluoromethyl)phosphonates through CuBr-mediated Tetsuo Murano, Kenji Suemune and cross coupling reactions of [(diethoxyphosphinyl)difluoromethyl]zinc bromide Shiroshi Shibuya with aryl iodides Hiroyasu Tsuge, Kensuke Takumi, Highly diastereoselective Michael addition to optically active tri- Tomoyuki Nagai, Takashi Oxano, fluoromethylated a,B-unsaturated sulfonamides based on their hinge-like Shoji Eguchi and Hiroshi Kimoto conformation Chiaki Kuroda, Hiroyuki Nogami, Stereochemistry of Lewis acid and fluoride promoted intramolecular Yuki Ohnishi, Yoshihiro Kimura and cyclization of B-(alkoxycarbonyijallyisilane with enones. Synthesis of James Y. Satoh bicyclo[4 3.0}nonanes Adam S.-Y. Lee and Wen-Chin Dai A faciie and highly efficient sonochemical synthesis of organostannane via Barbier reaction Yoshihide Matsuo, Ryoichi Ishida, Yendolipin, a novel lipobetaine with an inhibitory activity toward Takeshi Matsumoto, morphogenesis in a foliaceous green alga Monostroma oxyspermum Masakazu Tatewaki and Minoru Suzuki Junko Yamada, Masuo Morisaki, 24-Methyl- and 24-ethyl-A****)-cholesterols as immediate biosynthetic Keisuke Iwai, Hiroki Hamada, precursors of 24-alkylsterols in higher plants Naoko Sato and Yoshinori Fujimoto Shuntaro Mataka, Jiang Ma, Diels-Alder reaction of anthraceno[3.3jortho-benzophane and -naph- Thies Thiemann, thophane. Control of n-facial diastereoselectivity by underlying n-systems Jerzy M. Rudzifski, Hirohisa Tsuzuki, Tsuyoshi Sawada and Masashi Tashiro 192 Tetrahedron Yutaka Watanabe, Synthesis of 2,6-di-O-a-D-mannopyranosyiphosphatidyl-D-myo-inositol. Takashi Yamamoto and Utilization of glycosylation and phosphorylation based on phosphite Tadashi Okazaki chemistry Laurant Lemee, Evelyne Peuchant, Deinoxanthin: a new carotenoid isolated from Deinococcus radiodurans Michel Clerc, Martin Brunner and Hanspeter Pfander Cornelia Schroeder, Inverse correlated 'H—-'°C in vivo NMR as a probe to follow the metabolism Jiirgen Sommer, Eberhard Humpfer of unlabeled vanillin by plant cell cultures and Joachim Stéckigt Olaf Rotthaus, Doris Kriger, Reductions of keto esters with bakers yeast in organic solvents—a Martin Demuth and Kurt Schaffner comparison with the results in water Rolf Huisgen and Jochen Rapp 1,3-Dipolar cycloadditions—XCVIII. The chemistry of thiocarbony! S-sulfides Jochen Rapp and Rolf Huisgen Diels—Alder reactions of diaryl thioketones with dienophiles Gerhard Kretzschmar, Chemistry and biological activity of oasomycin macrolactones Manfred Krause and Lajos Radics Jean-Yves Mérour, Ahmed Mamai, Heterodiene cycloadditions: synthesis and oxidation of pyrano[3,2-bjindoles Béatrice Malapel and into spiro derivatives Philippe Gadonneix Siméon Arseniyadis, Formal total synthesis of an A-seco mevinic acid Rosemeire Brondi-Alves, Dmitry V. Yashunsky, Pierre Potier and Loic Toupet istvan E. Marko, Paul R. Giles and Catalytic enantioselective Baylis—Hillman reactions. Correlation between Nigel J. Hindley pressure and enantiomeric excess Renzo Rossi, Fabio Bellina and Selective palladium-mediated carbon—oxygen bond and carbon—sulfur bond Luisa Mannina forming reactions which involve functionalized C,,,-hybridized halides or triflates and C,,-hybridized halides Mohammad M. Al-Arab, The Michael reaction of acetophenones with trans-dibenzoylethylene Mohammad A. Atfeh and Fowzia S. Al-Saleh Michat Fedory/rski, Phase transfer catalyzed (PTC) reactions of chloroform with alkenyl Magdalena Kubicka-Prusik, carboxylates. Effect of catalyst structure on reaction course Maigorzata Kursa and Andrzej Joniczyk Philip C. Bulman Page, Mark Purdie Regioselective and stereoselective 1,3-dipolar addition of nitrile oxides to 2- and David Lathbury crotyl-1,3-dithiane 1-oxides Laszi6 Lazar, Attila G. Lakatos, Five-component equilibria of ring-chain tautomeric mixtures derived from 3- Ferenc Filép, Gabor Bernath and amino-1,2-propanediol and aromatic aldehydes Frank G. Riddell Francesco Risitano, 5-exo-Trigonal cyclization and [3,5] rearrangement of N-aryl benzamidoximes Giovanni Grassi, Francesco Foti by reaction with nitrile oxides and Fabrizio Filocamo Juma’a R. Al Dulayymi, Synthesis of putative A®-, A’®- and A'*-desaturase inhibitors Mark S. Baird, Cynthia M. Dale, Brendan J. Grehan and M. Fiona Shortt Raymond C. F. Jones, Condensation reactions of 4,5-dihydroimidazoles: preparation and conjugate John S. Snaith, additions of 2-alkenyl-4,5-dihydroimidazoles Michael W. Anderson and Mark J. Smaliridge Manoor V. Anuradha and Acylation of unprotected amino acids using ultrasound Bhagavathula Ravindranath Jesuraja Bosco Bharathy, Homogeneous catalysis in the Cr(V) oxidation of organic sulfides Tharumeya Kuppusamy Ganesan, Ambalam Ibrahim Ali Mohammed Sheriff and Seenivasan Rajagopal Tahir M. Kasumov, Valery K. Brel, Oxidative properties of xenon (Il) compounds. A new, convenient synthesis Yuri K. Grishin, Nikolai S. Zefirov of [bis(trifluoroacetoxy)iodojarenes, [bis(trifluoroacetoxy)iodojperfluoroalk- and Peter J. Stang anes and p-oxo-bridged aryliodoso-derivatives Christopher J. Easton and Stereoselective synthesis of (2S,3S)-y-hydroxyvaline utilising an asymmetric Martin C. Merrett radical hydrogen bromide addition Tetrahedron Maurizio D'Auria, Eliana De Luca, Photochemical synthesis of dipyrryimethane derivatives Vittorio Esposito, Giacomo Mauriello and Rocco Racioppi Paola Ciapetti, Francesco Soccolini Synthesis of N-Fmoc-a-amino acids carrying the four DNA nucleobases in and Maurizio Taddei the side chain Instructions to Contributors NUMBER 4 Contents Contributors to this Issue Graphical Abstracts Corrigendum TETRAHEDRON REPORT NUMBER 412 Anastasios Varvoglis Chemical transformations induced by hypervalent iodine reagents ARTICLES Alan P. Marchand, Yanjun Wang, Oxidative functionalization of unactivated carbon—hydrogen bonds in Sulejman Alihodzic and heptacyclo[6.6.0.0*°.0*'*.0*''.0°*.0'° “*}tetradecane (HCTD) Derek H. R. Barton Masahiro Kako, Masahiro Mori, Charge-transfer complex formation and photo-induced electron-transfer Kaname Hatakenaka, Seiji Kakuma, reaction of dibenzo-7-silabicyclo[2.2.1]}hepta-2,5-dienes Yasuhiro Nakadaira, Masanori Yasui and Fujiko Iwasaki Hirofumi Matsunaga, Chiral electrophilic ‘glycinal’ equivalents. New synthons for optically active a- Tadao Ishizuka and amino acids and 4-substituted 2-oxazolidinones Takehisa Kunieda Andreas Schmidt and Charge-cumulated hetarenes—1. (Pyrimidin-2,4,6-triyl)-tris-hetarenium salts Annemarie Hetzheim Jérg Junggebauer and An improved synthesis of a polymer-supported distannane and its application Wilhelm P. Neumann to radical formation René Csuk, Martin Kihn and Easy access to C-glycosides from aldonolactones by a Claisen-type chain- Dieter Stréhi extension reaction Catherine Leriverend, Thiophilic addition of organolithiums to trithiocarbonate oxides (sulfines). Patrick Metzner, Synthesis of B-oxoketene dithioacetals, 1,4-dicarbonyl compounds, and allyl Antonella Capperucci and sulfoxides Alessandro Deg|’Innocenti Alain Favre-Réguillon, Polymeric and immobilized crown compounds, material for ion separation Nathalie Dumont, Branko Dunjic and Marc Lemaire Angela Patti, Daniela Lambusta, Lipase-assisted preparation of enantiopure ferroceny! sulfides possessing Mario Piattelli, Giovanni Nicolosi, planar chirality and their use in the synthesis of chiral sulfoxides Patrick McArdle, Desmond Cunningham and Martin Walsh Guo-giang Lin and Zhi-cai Shi Enantiomerically pure cage-shaped (1S,4.S,5A)-4-hydroxy-2,6-diazabicyclo- [3.3.0Joctane and (1S,4A,5A)-4-hydroxy-2-oxa-6-azabicyclo[3.3.0Joctane: synthesis and test for enantioselective catalysis Polonca TrebSe, Slovenko Polanc, Selective and efficient transformation of 5,6,7,8-tetrahydro-2H-1-benzopyran- Marijan Koéevar, Tomaz Solmajer 2,5-diones with hydrazines to 5-hydrazono-2H-1-benzopyran-2-ones and and Simona Golié Grdadoinik quinoline-2,5-diones. Extension to related systems Josefina Quirante, Synthesis of 2-azabicyclo[3.3.1]nonanes by means of (carbamoyl)dichloro- Carmen Escolano, Mireia Massot methyl radical cyclization and Josep Bonjoch Mar Ramos, Ibon Alkorta and The Mills—Nixon effect on enol—enoi tautomerism in B-dicarbonyl compounds José Elguero and on annular tautomerism in NH-pyrazoles: a semi-empirical study 194 Tetrahedron Ramon Badorrey, Carios Cativiela, Reversal of the stereochemical course of the addition of phenyimagnesium Maria D. Diaz-de-Villegas and bromide to N-benzylimines derived from A-glyceraldehyde depending on the José A. Galvez O-protecting group and its application to the synthesis of both enantiomers of phenyiglycine Paolo Crotti, Valeria Di Bussolo, Regiochemical control of the ring opening of aziridines by means of chelating Lucilla Favero and Mauro Pineschi processes—|. Synthesis and ring-opening reactions of aziridines derived from 5,6-dihydro-2H-pyran and of the diastereoisomeric cis- and trans-azi- ridines derived from 3-(benzyloxy)cyclohexene, 2-(benzyloxy)-3,6-dihydro-, and 2-(benzyloxy)-6-methy!-3,6-dihydro-2H-pyran A. Srikrishna, D. Vijaykumar and Enantiospecific synthesis of (+)-dihydroerythrodiene, (+)-dihydrospirojatamol T. Jagadeeswar Reddy and (+)-dihydroepispirojatamol! Fabiana D’Anielio, André Mann, Stereoconvergent synthesis of (2S,3S,8S,9S,4E,6E)-N-Boc-ADDA starting Angéle Schoenfelder and from (S)-serine and (S)-phenyllactic acid Maurizio Taddei Elson Santiago de Alvarenga, An unexpected photoadduct of N-carbomethoxymethylpyrrolidine with a Christine J. Cardin and John Mann chiral butenolide and benzophenone: X-ray structure and synthetic utility Orazio A. Attanasi, Synthesis and reactions of some nitrone derivatives Paolino Filippone and Chiara Fiorucci Manuela Ballabio, 2,2,6- and 2,3,5-Trimethylpiperazines as monocyclic analogues of the p- Daniela Bariocco, opioid agonist 3,8-diazabicyclo[3.2.1]octanes: synthesis, modeling, and Giorgio Cignarella, Diego Colombo activity and Lucio Toma Margherita Gavagnin, Nicon Ungur, Novel verrucosins from the skin of the mediterranean nudibranch Doris Francesco Castelluccio and verrucosa Guido Cimino Geoffrey T. Crisp and Jeffrey Gore Preparation of biological labels with acetylenic linker arms Geoffrey T. Crisp and Jeffrey Gore Palladium-catalysed attachment of labels with acetylenic linker arms to biological molecules Tetrahedron Reports on Organic Chemistry instructions to Contributors NUMBER 5 Contents Contributors to this Issue Graphical Abstracts Corrigenda Thomas T. Shawe, Addition reactions of cyclic s-trans-enaminones with Grignard reagents Darren B. Hansen, Kelly Ann Peet, Anthony S. Prokopowicz, Patrice M. Robinson, Annatina Cannon, Kathleen E. Dougherty, Andrew A. Ross and Linda M. Landino John W. Huffman, Side chain methy! analogues of A*-THC Julia A. H. Lainton, W. Kenneth Banner, Sammy G. Duncan, Jr, Robert D. Jordan, Shu Yu, Dong Dai, Billy R. Martin, Jenny L. Wiley and David R. Compton George G. Harrigan, Kailuins A—D, new cyclic acyidepsipeptides from cultures of a marine-derived Beth L. Harrigan and bacterium Bradley S. Davidson Tetrahedron 195 Ashok D. Patil, Alan J. Freyer, Pulcherrimins A—D, novel diterpene dibenzoates from Caesalpinia pulcher- R. Lee Webb, Gary Zuber, rima with selective activity against DNA repair-deficient yeast mutants Rex Reichwein, Mark F. Bean, Leo Faucette and Randall K. Johnson Hideharu Suzuki, Chiemi Iwata, A general synthetic route for 1-substituted 4-oxygenated B-carbolines Katsumi Sakurai, (synthetic studies on indoles and related compounds—xXL1) Kazuhiko Tokumoto, Hiroko Takahashi, Masako Hanada, Yuusaku Yokoyama and Yasuoki Murakami Hiroshi Morita, Takashi Kayashita, Conformation of cyclic heptapeptides: solid and solution state conformation Koichi Takeya, Hideji Itokawa and of yunnanin A Motoo Shiro Hiroshi Morita, Akira Gonda, Cycloleonuripeptide D, a new proline-rich cyclic decapeptide from Leonurus Koichi Takeya, Hideji Itokawa and heterophyllus Yoichi litaka Yuichi Kobayashi, Eisuke Takahisa, Reduction of carbonyl compounds by using polymethylhydrosiloxane: Miwa Nakano and Kengo Watatani reactivity and selectivity Masaharu Kume, Hiroaki Ooka and Efficient and practical synthesis of 1B-methyicarbapenems Hiroyuki Ishitobi Philippe BGhimann, Strong hydrogen bond-mediated complexation of H,PO, by neutral bis- Seiichi Nishizawa, Kang Ping Xiao thiourea hosts and Yoshio Umezawa Gerhard Bringmann, Quantum chemical! calculation of CD spectra: the absolute configuration of Stefan Busemann, Karsten Krohn palmarumycins CP, and C, and Karsten Beckmann Olaf Ritzeler, Lothar Hennig, Search for new moenomycin structure—activity relationships. Synthesis of a Matthias Findeisen, Peter Weizel trisaccharide precursor of a moenomycin analogue and Dietrich Miller Olaf Ritzeler, Lothar Hennig, Synthesis of a trisaccharide analogue of moenomycin A,,. Implications of Matthias Findeisen, Peter Weizel, new moenomycin structure—activity relationships Dietrich Miller, Astrid Markus, Guy Lemoine, Maxime Lampilas and Jean van Heijenoort Gerhard Range, Ralf Krahmer, A chemoenzymatic approach towards moenomycin structural analogues Peter Weizel, Dietrich Miller, Guido F. Herrmann, Udo Kragl, Christian Wandrey, Astrid Markus, Yveline van Heijenoort and Jean van Heijenoort Frank RGbsam, Antje M. Evers, Z-Selective olefination of base-sensitive chiral B-hydroxy-a-aminoaldehydes Christoph Michel and using a modified Horner—-Wadsworth-Emmons reaction Athanassios Giannis Edwin C. Constable and A convergent approach to a solubilised septipyridine Diane R. Smith Rachid Barhdadi, Blandine Simsen, Direct electroreduction or use of an electrogenerated base: two ways for the Michel Troupe! and coupling of polyhalogenated compounds with aldehydes or ketones Jean-Yves Nédélec Thomas Ryckmans, 5-Aminopyrazoles from enolisable ketones and 1-cyano-1-alkyihydrazines Heinz-Gunter Viehe, Janine Feneau-Dupont, Bernard Tinant and Jean-Paul Declercq Manfred Schlosser and 2-Ethoxyvinyllithiums and diethoxyvinyllithiums: What makes them stable or Heng-xu Wei fragile? Nataly Bontemps, Total synthesis of the marine pentacyclic alkaloid meridine Evelyne Delfourne, Jean Bastide, Christian Francisco and Franz Bracher Vania Armani, Carlo Dell’Erba, Synthetic exploitation of the ring-opening of 3,4-dinitrothiophene—VII. Access Marino Novi, Giovanni Petrillo and to disubstituted 1,2,5-oxadiazole-2-oxides and 2-phenyl-2H-1,2,3-triazole-1- Cinzia Tavani oxides 196 Tetrahedron Giovanni Poli, Elisa Maccagni, Diastereoselective addition of metai-coordinated and ‘naked’ nucleophilic Leonardo Manzoni, Tullio Pilati and reagents to norephedrine derived 2-acyl-N-tosyl-oxazolidines Carlo Scolastico Anniken T. Overas, Lewis acid mediated Diels—Alder reactions of 6-vinyipurines Lise-Lotte Gundersen and Frode Rise Paolo Quadreili, Cycloadditions of nitrile oxides to amidoximes. A general synthesis of 3,5- Anna Gamba Invernizzi, disubstituted 1,2,4-oxadiazole-4-oxides Mario Falzoni and Pierluigi Carameliia Vyachesiav |. Krasnov, Transformations of perfluoroxylenes and perfiuoro-p-cymene under the Vyacheslav E. Platonov, action of Zn(Cu)—-DMF-H,O irina V. Beregovaya and Lyudmila N. Shchegoleva Hisham A. Abd El-Nabi Novel heterocycles: a convenient synthesis of pyrrolo[2,3-djpyrazole; cyclo- addition reaction of N-aryi(methyl)pyrrol-2,3-diones to diazomethane and olefins Pablo Asenjo, Francisco Farina, Polycyclic hydroxyquinones—XXIX. Regioselective reactions of 5-sulphur- M. Victoria Martin, substituted furan-2(5H)-one anions with naphthoquinone monoketals M. Carmen Paredes and Application to the synthesis of anthracyclinone precursors J. Javier Soto Maria Luisa Geimi, 5(4H)-Oxazolones—X. Acid and base effects on the transiactonization Francesca Clerici and reaction of 4-(2-oxa-alkylidene)-5(4H)-oxazolones: new synthesis of 5- Alessandra Melis alkylidene-3-benzoylamino-2(5H)-furanones Parthasarathy Saravanan, Studies in the rearrangement of epoxides with lithium dialkylamide—ithium Arpita DattaGupta, tert-butoxide Debnath Bhuniya and Vinod K. Singh Johanna Wachtmeister, Synthesis of carbocyclic 2',3'-dideoxy-2'-fluoro-3'-C-hydroxymethy! nucleo- Bjérn Classon, Bertil Samuelsson side analogues as potential inhibitors of HIV and HSV and Ingemar Kvarnstrém Mircea Darabantu, Gerard Pié, Synthesis and stereochemistry of some heterocyclic saturated compounds Sorin Mager, Eleonora Cotora, based on /-p-nitrophenyiserinol skeleton—!. Ring—chain tautomerism of some Luiza Gaina, Loredana Costas and Schiff bases of /-p-nitrophenylserinol Adrian Mates Mircea Darabantu, Gerard Plé, Synthesis and stereochemistry of some heterocyclic saturated compounds Sorin Mager, Luiza Gaina, based on /-p-nitrophenylserinol skeleton—ll. 1-Aza-3,7-dioxabicyclo[{3.3.0]- Eleonora Cotora, Adrian Mates and octanes Loredana Costas Mircea Darabantu, Gerard Plé, Synthesis and stereochemistry of some heterocyclic saturated compounds Sorin Mager, Camelia Puscas and based on /-p-nitrophenylserino! skeleton—ill. 1,3-Dioxanic Schiff bases Eleonora Cotora Instructions to Contributors NUMBER 6 Contents Contributors to this Issue Graphical Abstracts Corrigendum TETRAHEDRON REPORT NUMBER 413 Reuben D. Rieke and New organometailic reagents using highly reactive metals Mark V. Hanson ARTICLES Qi Chao and Vasu Nair Synthesis of bicarbocyclic dideoxynucleosides as potential antiviral agents Dennis P. Curran and Can an aromatic ring alter the reactions of a nearby unsaturated imide? A Moon-Hwan Yoon study of the rate and selectivity of nitrile oxide cycloaddition reactions of acryloyl derivatives of the Rebek imide benzoxazole