Total synthesis of brevetoxin B

Isao Kadota, Hiroyoshi Takamura, Hiroki Nishii, Yoshinori Yamamoto

Research output: Contribution to journalArticle

56 Citations (Scopus)

Abstract

The convergent total synthesis of brevetoxin B (1) has been achieved. The intramolecular allylation of the O,S-acetal 20, prepared from the α-chlorosulfide 17 and the alcohol 5, was carried out using AgOTf as a Lewis acid to give the diene 21, predominantly. Ring-closing metathesis of 21 with the Grubbs catalyst 23 afforded the hexacyclic ether 25 which was converted to the A-G ring segment 2 through several steps. The intramolecular allylation of the α-acetoxy ether 42, prepared from 2 and the J-K ring segment 3, followed by ring-closing metathesis provided the polycyclic ether framework 44. A series of reactions of 44, including oxidation of the A ring, deprotection of the silyl ethers, and selective oxidation of the resulting allylic alcohol, furnished 1.

Original languageEnglish
Pages (from-to)9246-9250
Number of pages5
JournalJournal of the American Chemical Society
Volume127
Issue number25
DOIs
Publication statusPublished - Jun 29 2005
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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