Enantioselective Total Synthesis of (-)-Pavidolide B
- PMID: 28870073
- DOI: 10.1021/jacs.7b07388
Enantioselective Total Synthesis of (-)-Pavidolide B
Abstract
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 RhCl-catalyzed double bond isomerization to form the seven-membered D ring of (-)-pavidolide B.
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