Studies towards the synthesis of halomon: asymmetric hexafunctionalisation of myrcene

Chem Commun (Camb). 2014 Nov 18;50(89):13725-8. doi: 10.1039/c4cc06234e.

Abstract

A novel dihydroxylation-dibromination-dihydroxylation sequence employing in situ protection of diols as boronate esters during the dihydroxylation reactions provides the first enantiomerically pure hexafunctionalised myrcene derivative. This concise four-step asymmetric sequence provides an advanced intermediate for the targeted synthesis of halomon via stereospecific transformations, where both stereogenic centres of the natural product have been set.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acyclic Monoterpenes
  • Alkenes / chemistry*
  • Halogenation
  • Hydrocarbons, Halogenated / chemistry*
  • Hydroxylation
  • Monoterpenes / chemistry*

Substances

  • Acyclic Monoterpenes
  • Alkenes
  • Hydrocarbons, Halogenated
  • Monoterpenes
  • 6-bromo-3-(bromomethyl)-7-methyl-2,3,7-trichloro-1-octene
  • myrcene