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Updated: Mar 7, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Unified Total Synthesis of Madangamines A, C, and E
Takahiro Suto1, Yuta Yanagita1, Yoshiyuki Nagashima1
1Department of Applied Chemistry, Faculty of Science and Technology, Keio University , 3-14-1, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
Abstract:
A stereodivergent strategy for the synthesis of skipped dienes is developed. The method consists of hydroboration of allenes and Migita-Kosugi-Stille coupling, which allows for access to all four possible stereoisomers of the skipped dienes. The hydroboration is especially useful for providing both E-allylic and Z-allylic alcohols from the same allene by simply changing the organoborane reagent. The strategy was successfully applied to a unified total synthesis of the madangamine alkaloids via a common ABCE-tetracyclic intermediate with a (Z,Z)-skipped diene. The late-stage variation of the D-ring enabled the supply of synthetic madangamines A, C, and E for the first time.
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