First total synthesis of (−)-aplyolide A

Abstract

The first total synthesis of (−)-aplyolide A † † Unfortunately the trivial name aplyolide A has previously been used for a sesterpene with a completely different structure: Crews, P.; Jimenez, C.; O'Neil-Johnson, M. Tetrahedron 1991, 47, 3585. , (16 S)-methyloxacyclohexadeca-(5 Z,8 Z,11 Z,14 Z)-tetraen-2-one, 1 is reported. The synthesis is based on three consecutive couplings of terminal alkynes with propargylic halides and proves the absolute configuration of the stereogenic center of the natural product.