Total synthesis of (+)-monocerin via tandem dihydroxylation-SN2 cyclization and a copper mediated tandem cyanation–lactonization approach?

Organic & Biomolecular Chemistry Pub Date: 2014-05-29 DOI: 10.1039/C4OB00965G

Abstract

A simple and novel synthesis of (+)-monocerin was achieved in 15 steps and 15.5% overall yield from 3-buten-1-ol employing hydrolytic kinetic resolution, Julia olefination, intramolecular tandem Sharpless asymmetric dihydroxylation-SN2 cyclization and a novel copper mediated tandem cyanation–cyclization as the key steps.

Graphical abstract: Total synthesis of (+)-monocerin via tandem dihydroxylation-SN2 cyclization and a copper mediated tandem cyanation–lactonization approach
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