Theoretical investigation of the rubicordifolin cascade

Org Lett. 2010 Nov 19;12(22):5162-5. doi: 10.1021/ol102157d. Epub 2010 Oct 25.

Abstract

The results of a theoretical investigation on the complex cascade reaction leading to the natural product rubicordifolin are reported. These computations analyze the discrete transformations that are required during the conversion of the vinyl naphthoquinone starting material into the natural product, including two pseudopericyclic cyclizations as well as a diastereoselective, hetero-Diels-Alder reaction.

Publication types

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

MeSH terms

  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Catalysis
  • Cyclization
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Models, Molecular*
  • Molecular Structure
  • Naphthols / chemical synthesis*
  • Naphthols / chemistry
  • Plants, Medicinal / chemistry
  • Pyrones / chemical synthesis*
  • Pyrones / chemistry
  • Rubia / chemistry
  • Stereoisomerism

Substances

  • Biological Products
  • Furans
  • Naphthols
  • Pyrones
  • furomollugin
  • rubicordifolin