No abstract

The first asymmetric total synthesis of a 16-membered macrolide, aspergillide D, is described. The chiral centers of the acid are derived from d-ribose and the alcohol subunit from 1,8-octane diol through Sharpless kinetic resolution, respectively. The other key reactions include Yamaguchi esterification, ring-closing metathesis reaction, and Shiina macrolactonization to construct the fully functionalized macrocycle.

A simple and an efficient synthesis of (+)-sacrolide A has been achieved from a known compound 10 in 12 steps with 9% overall yield. Key steps involved are Jacobsen's hydrolytic kinetic resolution, Sharpless asymmetric epoxidation, transselective hydrometallation of the propargylic alcohol, and acidcatalyzed Kita macrolactonization.

The stereoselective total synthesis of oxylipin macrolide (+ +)-sacrolide Aw as achieved in a1 3l ongest linear step sequence with 12.1 %o verall yield. The key reactions are Jacobsen'sh ydrolytic kinetic resolution,S harpless asymmetric epoxidation, Yamaguchi esterification and intramolecular Nozaki-Hiyama-Kishi (NHK) macrocyclization to construct the required 14-memberedl actone.