Total synthesis of (+)-monocerin via tandem dihydroxylation-S(N)2 cyclization and a copper mediated tandem cyanation-lactonization approach.

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.