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Updated: Mar 16, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Substrate-Controlled Asymmetric Total Synthesis and Structure Revision of (-)-Bisezakyne A
Iljin Shin1, Dongjoo Lee1, Hyoungsu Kim1
1College of Pharmacy and Research Institute of Pharmaceutical Science and Technology (RIPST), Ajou University , Suwon 16499, Republic of Korea.
Abstract:
The first asymmetric total synthesis and subsequent structure revision of (-)-bisezakyne A, a Laurencia C15 acetogenin from Alpysia oculifera, has been accomplished. Our substrate-controlled synthesis of this oxolane natural product features a highly stereoselective "protecting-group-dependent" intramolecular amide enolate alkylation strategy for the synthesis of the key 9,10-trans-9,12-cis-10-hydroxytetrahydrofuran intermediate through "nonchelate" control. In addition, our synthesis determined the absolute configuration of the halogenated marine natural product.
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