Total Synthesis of Gambierol, a Marine Polycyclic Ether

Haruhiko Fuwa, Makoto Sasaki

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

The first total synthesis of gambierol, a marine polycyclic ether toxin, has been achieved. Highly efficient synthesis of the ABC and EFGH ring fragments allowed us to prepare those two advanced intermediates in multi-gram quantities. The key feature of the present total synthesis is the B-alkyl Suzuki-Miyaura coupling tactics, which culminated in the union of the advanced intermediates and convergent synthesis of the octacyclic polyether core. Introduction of the sensitive triene side chain via Pd(PPh3) 4/CuCl/LiCl-promoted Stille coupling was conducted at the final step of the synthesis. The present total synthesis supplied useful quantities of gambierol and its structural analogues for detailed biological studies: an interesting observation was gained through pathological studies. Also, preliminary structure-activity relationship studies revealed that the functionalities present in the H ring and unsaturated side chain are crucial for notent toxicitv asainst mice.

Original languageEnglish
Pages (from-to)742-751
Number of pages10
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume61
Issue number8
DOIs
Publication statusPublished - 2003 Aug

Keywords

  • B-alkyl Suzuki-Miyaura coupling
  • Ciguatera
  • Ciguatoxin
  • Gambierol
  • Marine toxin
  • Pathological studies
  • Polycyclic ethers
  • Stille reaction
  • Structure-activity relationship
  • Total synthesis

ASJC Scopus subject areas

  • Organic Chemistry

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