Total Synthesis of SacrolideA by Following a Nozaki-Hiyama-Kishi Macrocyclization Strategy

Abstract

The stereoselective total synthesis of oxylipin macrolide (+)-sacrolideA was achieved in a 13 longest linear step sequence with 12.1% overall yield. The key reactions are Jacobsen's hydrolytic kinetic resolution, Sharpless asymmetric epoxidation, Yamaguchi esterification and intramolecular Nozaki-Hiyama-Kishi (NHK) macrocyclization to construct the required 14-membered lactone. Sacr' bleu! A highly stereoselective total synthesis of sacrolideA has been achieved in a convergent and efficient manner by utilizing Nozaki-Hiyama-Kishi macrocyclization as the key reaction.