Towards the diastereoselective synthesis of derivative of 11′-epi-brevipolide H?

Organic & Biomolecular Chemistry Pub Date: 2014-01-08 DOI: 10.1039/C3OB42367K

Abstract

An efficient diastereoselective synthesis of brevipolide H derivative is described. The approach features the use of (i) catalytic asymmetric transfer hydrogenation, (ii) hydroxyl-directed cyclopropanation, and (iii) substrate-controlled catalytic epoxidation and ring-closing metathesis. Remarkably, in this convergent synthesis process, stereogenic centers were installed through catalytic reactions with high stereocontrol, which greatly facilitates the synthesis of stereo-divergent derivatives.

Graphical abstract: Towards the diastereoselective synthesis of derivative of 11′-epi-brevipolide H
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