Total syntheses of multicaulins via oxidative photocyclization of stilbenes

J Nat Prod. 2014 Sep 26;77(9):2134-7. doi: 10.1021/np5001158. Epub 2014 Aug 20.

Abstract

The Wittig reaction of 3-isopropyl-4-methoxybenzaldehyde and 2,3-dimethylbenzylphosphonium bromide afforded the corresponding stilbene mixture 16. Oxidative photocyclization of stilbene 16 with iodine facilitated the first total synthesis of 7-isopropyl-6-methoxy-1,2-dimethylphenanthrene, multicaulin (1). The O-demethylation of 1 with BBr3 afforded the 7-isopropyl-1,2-dimethylphenanthren-6-ol, O-demethylmulticaulin (2).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzaldehydes / chemistry*
  • Cyclization
  • Molecular Structure
  • Organophosphorus Compounds / chemistry*
  • Oxidation-Reduction
  • Phenanthrenes / chemical synthesis*
  • Phenanthrenes / chemistry
  • Stilbenes / chemistry*

Substances

  • 2,3-dimethylbenzylphosphonium bromide
  • 3-isopropyl-4-methoxybenzaldehyde
  • Benzaldehydes
  • Organophosphorus Compounds
  • Phenanthrenes
  • Stilbenes
  • multicaulin