Asymmetric Total Synthesis of (+)-Neooxazolomycin Using a Chirality-Transfer Strategy

Abstract

The total synthesis of (+)-neooxazolomycin was achieved from the amino-acid d-serine. The efficiency of this approach is derived from the use of principles of memory of chirality and dynamic kinetic resolution in the intramolecular aldol reaction of a serine derivative to build the densely functionalized lactam framework and to install three contiguous stereocenters. The key intermediate was readily elaborated to the target natural product.

Keywords: alkaloids; asymmetric synthesis; diastereoselectivity; natural products; total synthesis.