Concise Total Synthesis of Nannocystin A

• DOI: 10.1002/ange.201606679
• Publication Date: 2016-09-16T09:34:28Z
• Authors: Linping Liao; Jingjing Zhou; Zhengshuang Xu; Tao Ye
• Keywords: Macrocyclic Compounds; Molecular Structure; Stereoisomerism; 01 natural sciences; 0104 chemical sciences

AbstractNannocystin A, a structurally unique 21‐membered macrocyclic depsipeptide with low nanomolar inhibitory activity against elongation factor 1A, was synthesized according to a strategy involving the vinylogous Mukaiyama aldol reaction, Sharpless epoxidation, olefin metathesis, the Mitsunobu reaction, and a palladium‐catalyzed intramolecular Suzuki coupling of a highly complex cyclization substrate. The overall synthesis is efficient and paves the way for preparation of analogues for drug development efforts.