Stereospecific cis- and trans-ring fusions arising from common intermediates

Proc Natl Acad Sci U S A. 2014 Jun 3;111(22):7931-5. doi: 10.1073/pnas.1407613111. Epub 2014 May 19.

Abstract

Highly concise and stereospecific routes to cis and trans fusion, carrying various functionality at one of the bridgehead carbons, have been accomplished.

Keywords: Diels–Alder cycloaddition; angular methylation; cyclobutenone; mechanistic studies.

Publication types

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

MeSH terms

  • Alkylation
  • Cycloaddition Reaction / methods*
  • Cyclobutanes / chemistry*
  • Drug Industry / methods
  • Estrogens / chemical synthesis*
  • Methylation
  • Models, Molecular
  • Norsteroids / chemical synthesis*
  • Stereoisomerism*

Substances

  • Cyclobutanes
  • Estrogens
  • Norsteroids
  • cyclobutenone