Total synthesis and absolute stereochemistry of integric acid

J Org Chem. 2009 Nov 20;74(22):8878-81. doi: 10.1021/jo901845r.

Abstract

An efficient total synthesis of integric acid is described starting from the Wieland-Miescher ketone. Key steps involve a one-step orthogonal deprotection/protection strategy of a thioacetal/aldehyde and the selective oxidative cleavage of a prenyl group in the presence of two other unsaturated moieties. The synthesis of both C4' diastereoisomers of integric acid delivered unambiguous evidence for (S)-stereochemistry at the C4' position.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carboxylic Acids / chemical synthesis*
  • Carboxylic Acids / chemistry
  • Molecular Conformation
  • Naphthalenes / chemical synthesis*
  • Naphthalenes / chemistry
  • Stereoisomerism

Substances

  • Carboxylic Acids
  • Naphthalenes
  • integric acid