Total synthesis of (+/-)-mitorubrinic acid

Org Lett. 2006 Aug 3;8(16):3481-3. doi: 10.1021/ol0610993.

Abstract

[reaction: see text] (+/-)-Mitorubrinic acid, a member of the azaphilone family of natural products, has been constructed in 12 steps. Key aspects of the synthesis include elaboration and oxidative dearomatization of an isocoumarin intermediate to provide the azaphilone nucleus with a disubstituted, unsaturated carboxylic acid side chain.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Benzoates / chemical synthesis*
  • Benzoates / chemistry
  • Carboxylic Acids / chemistry
  • Catalysis
  • Molecular Structure
  • Stereoisomerism

Substances

  • Benzoates
  • Carboxylic Acids
  • mitorubrinic acid