Synthesis of the A-D Ring System of the Gambieric Acids

Org Lett. 2015 Oct 2;17(19):4694-7. doi: 10.1021/acs.orglett.5b02093.

Abstract

The A-D fragment of gambieric acids A and C has been synthesized using an asymmetric Tsuji-Trost allylation reaction to couple the two key segments. The A ring fragment has been prepared by a short and highly efficient route involving diastereoselective Lewis acid mediated alkylation of an acetal. Iterative ring-closing metathesis reactions have been used to construct cyclic ethers and assemble the tricyclic B-D fragment.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Ciguatoxins / chemical synthesis*
  • Ciguatoxins / chemistry
  • Dinoflagellida / chemistry
  • Lewis Acids / chemistry
  • Marine Biology
  • Molecular Structure
  • Palladium / chemistry
  • Stereoisomerism

Substances

  • Lewis Acids
  • gambieric acid C
  • Ciguatoxins
  • gambieric acid A
  • Palladium