Access to the protoilludane core by gold-catalyzed allene-vinylcyclopropane cycloisomerization

Org Lett. 2013 Sep 6;15(17):4580-3. doi: 10.1021/ol402188b. Epub 2013 Aug 20.

Abstract

Gold(I)-catalyzed allene-vinylcyclopropane cycloisomerization leads to the tricyclic framework of the protoilludanes in a single step by a reaction that involves a cyclopropane ring expansion and a Prins cyclization.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkadienes / chemistry
  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Catalysis
  • Cyclization
  • Cyclopropanes / chemistry
  • Gold / chemistry*
  • Isomerism
  • Molecular Structure
  • Polycyclic Sesquiterpenes
  • Sesquiterpenes / chemical synthesis*
  • Sesquiterpenes / chemistry
  • Vinyl Compounds / chemistry

Substances

  • Alkadienes
  • Biological Products
  • Cyclopropanes
  • Polycyclic Sesquiterpenes
  • Sesquiterpenes
  • Vinyl Compounds
  • protoilludane
  • propadiene
  • Gold