Iron(III) catalyzed direct synthesis of cis-2,7-disubstituted oxepanes. The shortest total synthesis of (+)-isolaurepan

Org Lett. 2012 Dec 7;14(23):5904-7. doi: 10.1021/ol3028016. Epub 2012 Nov 20.

Abstract

Prins cyclization of bis-homoallylic alcohols with aldehydes catalyzed by iron(III) salts shows excellent cis selectivity and yields to form 2,7-disubstituted oxepanes. The iron(III) is able to catalyze this process with unactivated olefins. This cyclization was used as the key step in the shortest total synthesis of (+)-isolaurepan.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry
  • Aldehydes / chemistry
  • Alkenes / chemistry
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Cyclization
  • Iron Compounds / chemistry*
  • Laurencia / chemistry
  • Molecular Structure
  • Oxepins / chemical synthesis*
  • Oxepins / chemistry
  • Stereoisomerism

Substances

  • Alcohols
  • Aldehydes
  • Alkenes
  • Iron Compounds
  • Oxepins
  • isolaurepan