Approach to the Homoerythrina Alkaloids Using a Tandem N-Alkylation/Azomethine Ylide Cycloaddition Pearson, W. H.; Kropf, J. E.; Choy, A. L.; Lee, I. Y.; Kampf, J. W. J. Org. Chem.; 2007; 72(11); 4135-4148. Wipf group Current lit 08-18-07 Akira Nakamura Akira Nakamura @ Wipf Group 1 10/29/2007 Background Activities Curarelike Hypnotic Sedative Hypotensive Neuromuscular blocking CNS Akira Nakamura @ Wipf Group 2 10/29/2007 Target Alkaloids -Isolated from D. lenticellare Gillespie grown in the Fiji Islands in 1983. -There are no reports on pharmacological effect either 1 or 2. -Isolated alkaloids from D. lentivellare which include 3 are shown to have both cardiac effects in rats and molluscicidal activity. J. Nat. Prod. 1987, 50, 1041., Phytochemistry 1988, 27, 3789. Akira Nakamura @ Wipf Group 3 10/29/2007 Construction of the erythrinan ring system OMe OMe OMe NaN3 TFA, DCM O TMSO OMe O OMe 81% N OMe N MsO 3 J.d’Angelo, J. J. Org. Chem. 1993, 58, 2933 78% Padwa, A. Org. Lett. 2006, 8, 601. Akira Nakamura @ Wipf Group 4 10/29/2007 Retrosynthetic sequence Akira Nakamura @ Wipf Group 5 10/29/2007 Starting material synthesis a a Akira Nakamura @ Wipf Group 6 10/29/2007 Synthesis b b Akira Nakamura @ Wipf Group 7 10/29/2007 Key cycloaddition test Akira Nakamura @ Wipf Group 8 10/29/2007 2nd Retrosynthetic sequence Akira Nakamura @ Wipf Group 9 10/29/2007 2nd Key cycloaddition test c 1. c Akira Nakamura @ Wipf Group 10 10/29/2007