Formal enantioselective synthesis of nhatrangin A

Org Biomol Chem. 2020 Mar 11;18(10):1949-1956. 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.

Publication types

  • Research Support, Non-U.S. Gov't