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Formal enantioselective synthesis of nhatrangin A†
Sophie Feuillastre,Ludovic Raffier,Béatrice Pelotier,Olivier Piva
Organic & Biomolecular Chemistry Pub Date : 02/19/2020 00:00:00 , DOI:10.1039/C9OB02639H
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.

Graphical abstract: Formal enantioselective synthesis of nhatrangin A
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