Enantioselective total synthesis of (+)-rogioloxepane A

Org Lett. 2003 Aug 21;5(17):3009-11. doi: 10.1021/ol034923l.

Abstract

[reactiojn: see text] The enantioselective synthesis of (+)-rogioloxepane A has been achieved in 21 steps from 1,5-hexadien-3-ol. The key steps in the synthesis are an asymmetric glycolate alkylation leading to the diene 2 and a subsequent ring-closing metathesis to construct the oxepene core.

Publication types

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

MeSH terms

  • Alkadienes / chemistry
  • Alkylation
  • Glycolates / chemistry
  • Oxepins / chemical synthesis*
  • Oxepins / chemistry
  • Rhodophyta / chemistry
  • Stereoisomerism

Substances

  • Alkadienes
  • Glycolates
  • Oxepins
  • rogioloxepane A