Convergent synthesis of polycyclic ethers via the intramolecular allylation of α-acetoxy ethers and subsequent ring-closing metathesis

Isao Kadota, Akio Ohno, Kumiko Matsuda, Yoshinori Yamamoto

Research output: Contribution to journalArticle

68 Citations (Scopus)

Abstract

The Lewis acid mediated reaction of α-acetoxy ethers 15-22 gave the corresponding cyclized products 23, 25, 27, 29, 31, 32, 34, and 36 in good yields with high stereoselectivities. Those cyclized products were subjected to ring-closing metathesis to afford the polycyclic ethers 38-42, 44, and 45 in good yields. The usefulness of the present methodology was demonstrated by the convergent synthesis of the CDEF ring system of brevetoxin B (1) and the CDEFG ring system of gambierol (2).

Original languageEnglish
Pages (from-to)3562-3566
Number of pages5
JournalJournal of the American Chemical Society
Volume124
Issue number14
DOIs
Publication statusPublished - Apr 10 2002
Externally publishedYes

ASJC Scopus subject areas

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

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