Total synthesis of gambierol

Org Lett. 2002 Aug 22;4(17):2981-4. doi: 10.1021/ol026394b.

Abstract

[structure: see text] The first total synthesis of gambierol, a marine polycyclic ether toxin, has been achieved. The synthesis features the Pd(PPh3)4/CuCl/LiCl-promoted Stille coupling for the stereoselective construction of the sensitive triene side chain that includes a conjugated (Z,Z)-diene moiety.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Ciguatoxins*
  • Dinoflagellida / chemistry
  • Ethers, Cyclic / chemical synthesis*
  • Marine Toxins / chemistry
  • Palladium / chemistry
  • Polycyclic Compounds / chemical synthesis*
  • Polyenes / chemistry
  • Stereoisomerism
  • Vinyl Compounds / chemistry

Substances

  • Ethers, Cyclic
  • Marine Toxins
  • Polycyclic Compounds
  • Polyenes
  • Vinyl Compounds
  • gambierol
  • Ciguatoxins
  • Palladium
  • vinyl bromide