Asymmetric synthesis of the core structure of leucosceptroids A-D

J Org Chem. 2011 Aug 5;76(15):6169-76. doi: 10.1021/jo200899v. Epub 2011 Jun 28.

Abstract

The asymmetric synthesis of the core structure of leucosceptroids A-D has been achieved. The key steps of the synthesis includes the formation of the cis-2,5-disubstituted THF ring by TPAP catalytic oxidative cyclization followed by a highly diastereoselective intramolecular Diels-Alder reaction to fashion the fused tricyclic hydrindane ring system.

Publication types

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

MeSH terms

  • Catalysis
  • Cyclization
  • Heterocyclic Compounds, 3-Ring / chemical synthesis*
  • Heterocyclic Compounds, 3-Ring / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Oxidation-Reduction
  • Sesterterpenes / chemical synthesis*
  • Sesterterpenes / chemistry*
  • Stereoisomerism

Substances

  • Heterocyclic Compounds, 3-Ring
  • Sesterterpenes
  • leucosceptroid A
  • leucosceptroid B
  • leucosceptroid C
  • leucosceptroid D