Heteroatom-directed Wacker oxidations. A protection-free synthesis of (-)-heliophenanthrone

Org Biomol Chem. 2012 Apr 21;10(15):3060-5. doi: 10.1039/c2ob07095b. Epub 2012 Mar 7.

Abstract

The first enantioselective six-step synthesis of (-)-heliophenanthrone has been achieved without any protection-deprotection protocol at an overall yield of 28%. Key features of this synthesis comprise a heteroatom-directed Wacker oxidation of an internal cyclic olefin in addition to asymmetric Brown allylation and ring closing metathesis (RCM).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Oxidation-Reduction
  • Phenanthrenes / chemical synthesis*
  • Stereoisomerism

Substances

  • Phenanthrenes
  • heliophenanthrone