Asymmetric synthesis of naturally occurring nonenolide xyolide through cross metathesis and macrolactonization reaction

Abstract

Asymmetric total synthesis of xyolide, a small ring macrolide is presented in this article. The synthesis is achieved through an 'E' selective cross metathesis (CM) reaction between two appropriate fragments followed by lactonization by Shiina method. One of the fragments containing 7S,8S,9R stereocenters of xyolide is accessed from n-nonanal by adopting an organocatalytic asymmetric α-aminooxylation, Z-selective Ando olefination, and substrate directed dihydroxylation reaction. The other fragments containing 4S stereocenter was prepared by ME-DKR (metal enzyme combined dynamic kinetic resolution) method. © 2014 Elsevier Ltd. All rights reserved.