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Thursday, August 27 • 3:40pm - 4:00pm
[0090] Asymmetric Synthesis of Poison Dart Frog Indolizidine Alkaloids

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5-Substituted, 3,5-disubstituted, 5,8-disubstituted and 5,6,8-trisubstituted indolizidines belong to a group of alkaloids separated from the skin of poison dart frogs which lived in the tropical rainforest of Central and South America.  Some of these indolizidines have shown interesting AChEI activity which is important for the development of new drugs.

A series of substituted indolizidines, including 167B, 195G, 209B, 209D, 209I, 223A, 223AB, synthesized starting from tricyclic lactones will be discussed.  Key steps involved : 1) [3,3]-sigmatropic rearrangement to form tricyclic compounds with needed R1 substituent, 2) asymmetric alkylation/epimerization to obtain R2, 3) cyclization to form C7-C8 bond with R3 in correct stereochemistry, 4) construction of R4 (223AB case only), and 5) cleavage of the excess one carbon substituent on C5

ST Lecturers
avatar for Yu-Jang Li

Yu-Jang Li

Professor, National Chiayi University
Professor Department of Applied ChemistryNational Chiayi UniversityTaiwan 

Thursday August 27, 2015 3:40pm - 4:00pm PDT
Corwin West