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

Org Biomol Chem. 2014 Aug 21;12(31):5973-80. 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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chemistry, Organic / methods*
  • Copper / chemistry*
  • Cyanides / chemistry*
  • Cyclization
  • Hydroxylation
  • Isocoumarins / chemistry
  • Lactones / chemical synthesis
  • Lactones / chemistry*
  • Polyketides / chemistry
  • Stereoisomerism

Substances

  • Cyanides
  • Isocoumarins
  • Lactones
  • Polyketides
  • Copper
  • monocerin