Total synthesis of incarvilleatone and incarviditone: insight into their biosynthetic pathways and structure determination

Org Lett. 2012 Sep 21;14(18):4878-81. doi: 10.1021/ol302205w. Epub 2012 Sep 4.

Abstract

A concise biomimetic total synthesis of incarvilleatone and incarviditone is achieved in one pot via the highly stereoselective hetero- and homodimerization of (±)-rengyolone, respectively. The structure of incarviditone is revised on the basis of spectroscopic and computational evidence.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzofurans / chemical synthesis*
  • Benzofurans / chemistry*
  • Biosynthetic Pathways
  • Furans / chemistry*
  • Heterocyclic Compounds, 2-Ring / chemistry*
  • Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
  • Heterocyclic Compounds, 4 or More Rings / chemistry*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Stereoisomerism

Substances

  • Benzofurans
  • Furans
  • Heterocyclic Compounds, 2-Ring
  • Heterocyclic Compounds, 4 or More Rings
  • Rengyolone
  • incarviditone
  • incarvilleatone