Total synthesis of polycyclic ether natural products based on Suzuki-Miyaura cross-coupling

Makoto Sasaki, Haruhiko Fuwa

Research output: Contribution to journalReview articlepeer-review

87 Citations (Scopus)

Abstract

The polycyclic ether class of marine natural products presents formidable and challenging synthetic targets due to their structural complexity and exceptionally potent biological activities. We have developed a highly convergent strategy for the assembly of a huge polycyclic ether array, which features Suzuki-Miyaura cross-coupling of alkylboranes, generated from exocyclic enol ethers, with cyclic ketene acetal triflates or phosphates combined with reductive ring-closure. The utility of this strategy was demonstrated by its application to synthetic studies on ciguatoxins, and the total syntheses of gambierol and gymnocin-A.

Original languageEnglish
Pages (from-to)1851-1874
Number of pages24
JournalSynlett
Issue number11
DOIs
Publication statusPublished - 2004 Sep 6

Keywords

  • Cross-coupling
  • Natural products
  • Polycyclic ethers
  • Suzuki-Miyaura reaction
  • Total synthesis

ASJC Scopus subject areas

  • Organic Chemistry

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