Total Synthesis of (-)-Enigmazole B
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Updated: Jul 14, 2025

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Yoshihiro Goda1, Haruhiko Fuwa1
1Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan.
Abstract:
Total synthesis of (-)-enigmazole B was achieved for the first time. Highlights of the present synthesis include an olefin cross-metathesis and hemiacetalization/intramolecular oxa-Michael addition sequence for accessing an (E)-configured enol tosylate, a Sonogashira cross-coupling to assemble all the carbon atoms of the target natural product, a remarkably chemo- and regioselective Au-catalyzed intramolecular alkyne hydroalkoxylation for the construction of the dihydropyran ring, and a Yamaguchi macrolactonization to close the 18-membered macrolactone skeleton.
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