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Updated: Dec 27, 2025

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Formal enantioselective synthesis of nhatrangin A
Sophie Feuillastre1, Ludovic Raffier1, Béatrice Pelotier1
1Université de Lyon - Université Claude Bernard Lyon 1 - CNRS - INSA Lyon - CPE Lyon, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires - UMR 5246, équipe SURCOOF, Campus Lyon-Tech-La Doua, bât. Raulin, 43 Bd du 11 Novembre 1918, 69622 Villeurbanne Cedex, France. beatrice.pelotier@univ-lyon1.fr piva@univ-lyon1.fr.
Abstract:
A new and straightforward synthesis of the C1-C7 core fragment of nhatrangin A was achieved in 14 steps from achiral 3-hydroxybenzaldehyde, without the need of chiral reagents or enzymatic resolution to introduce the chiral centers. The key asymmetric steps include in particular a highly enantioselective organocatalyzed Michael addition on an aryl vinyl ketone, a Sharpless asymmetric epoxidation and a subsequent regioselective ring opening of the resulting chiral epoxide. This work represents the first formal enantioselective synthesis of nhatrangin A.
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