Synthesis of an F-H gambierol subunit using a C-glycoside-centered strategy

Org Lett. 2003 Mar 20;5(6):913-6. doi: 10.1021/ol034100w.

Abstract

[structure: see text] This manuscript describes our synthesis of the F-H subunit of gambierol. In addition to the synthesis of the tricycle, of note is an interesting protecting group influence on the generation of a C(23) C-glycoside as well as the use of ring-closing metathesis to generate a tetrasubstituted enol ether.

Publication types

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

MeSH terms

  • Animals
  • Ciguatoxins*
  • Cyclization
  • Dinoflagellida / chemistry*
  • Ethers, Cyclic / chemical synthesis*
  • Glycosides / chemistry*
  • Indicators and Reagents
  • Oxidation-Reduction
  • Polycyclic Compounds / chemical synthesis*

Substances

  • Ethers, Cyclic
  • Glycosides
  • Indicators and Reagents
  • Polycyclic Compounds
  • gambierol
  • Ciguatoxins