Sequential cycloaddition approach to the tricyclic core of vibsanin E. Total synthesis of (+/-)-5-epi-10-epi-vibsanin E

Org Lett. 2005 Dec 8;7(25):5561-3. doi: 10.1021/ol052005c.

Abstract

[chemical reaction: see text]. A direct access to (+/-)-5-epi-10-epi-vibsanin E is described, based on three key cycloaddition steps, a rhodium-catalyzed [4 + 3] cycloaddition, a heteronuclear [4 + 2] cycloaddition, and a photochemically induced [4 + 2] cycloaddition.

Publication types

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

MeSH terms

  • Catalysis
  • Cyclization
  • Diterpenes / chemical synthesis*
  • Diterpenes / chemistry
  • Molecular Structure
  • Photochemistry
  • Rhodium / chemistry*
  • Stereoisomerism

Substances

  • 5-epi-10-epi-vibsanin E
  • Diterpenes
  • Rhodium