Asymmetric synthesis of a 12-membered macrolactone core and a 6-epi analogue of amphidinolide W from 4-pentenoic acid

作者:Chatterjee Bhaskar; Mondal Dhananjoy; Bera Smritilekha*
来源:Tetrahedron: Asymmetry , 2012, 23(15-16): 1170-1185.
DOI:10.1016/j.tetasy.2012.07.006

摘要

A flexible and efficient asymmetric route to the synthesis of a 12-membered macrolactone core and a 6-epi analogue of amphidinolide W has been accomplished from commercially available 4-pentenoic acid. The successful generation of stereocenters was achieved by utilizing an Evans' chiral auxiliary-based alkylation and aldol reaction. Other key reactions such as a Julia-Kocienski olefination, Kita's macrolactonization, ring closing metathesis (RCM) reaction, and Yamaguchi's esterification were significant for the construction of the macrolactone cores.

  • 出版日期2012-8-31