Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

Enantioselective Total Synthesis of (−)-Pavidolide B

Enantioselective Total Synthesis of (−)-Pavidolide B
Yuan-He Li, Zhi-Ming Yan, Peng-Peng Zhang, Zhen Yang, Jian-Xian Gong
The enantioselective synthesis of (−)-pavidolide B (1) was achieved in a linear sequence of 10 steps. The key steps are (a) an enantioselective organocatalytic cyclopropanation; (b) a radical-based cascade annulation for the regio- and diastereo-selective synthesis of the highly functionalized lactone 3 bearing the characteristic tricyclic core and seven contiguous stereocenters; (c) a sequential ring-closing metathesis reaction and a RhCl3-catalyzed double bond isomerization to form the seven-membered D ring of (−)-pavidolide B.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b07388

DOI: 10.1021/jacs.7b07388

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