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Communication | Special issue | Vol 42, No. 1, 1996, pp.39-42
Published online, 1st January, 1970
DOI: 10.3987/COM-95-S8
An Asymmetric Synthesis of the Ant Venom Alkaloid (3S,5S,8aR)-3-Butyl-5-(4-pentenyl)indolizidine via the Sharpless Asymmetric Dihydroxylation

Hiroki Takahata, Hiroshi Bandoh, and Takefumi Momose

*Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, 2630 Sugitani, Toyama, Toyama 930-0194, Japan

Abstract

The first asymmetric synthesis of the ant venom alkaloid (3S,5S,8aR)-3-butyl-5-(4-pentenyl)indolizidine (1) has been performed by starting with the Sharpless asymmetric dihydroxylation of N-alkenylcarbamate (3) followed by reductive annulation (5-exotetrahedral).