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Updated: Jun 24, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Asymmetric total synthesis and stereochemical revision of gymnangiamide
Hitoshi Tone1, Marie Buchotte, Céline Mordant
1Laboratoire Charles Friedel, ENSCP Chimie ParisTech, UMR 7223, 11 rue P. et M. Curie, F-75231 Paris Cedex 05, France.
Abstract:
The asymmetric total synthesis of the originally proposed structure of gymnangiamide, a cytotoxic pentapeptide isolated from the marine hydroid Gymnangium regae Jaderholm, has been achieved. Key to the synthesis was the use of asymmetric hydrogenation of alpha-substituted beta-ketoesters through dynamic kinetic resolution for the preparation of nonproteinogenic chiral amino acids. The disparity of the NMR spectra between the synthetic material containing the L-serine residue and the natural product required a revision of the proposed structure.
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