Enantioselective synthesis of the medium ring ethers, tetrahydrooxepin, oxocane and hexahydrooxonin, of ciguatoxin. Extensive ring-expansion and chemoenzymatic desymmetrization strategy

Tohru Oishi, Megumi Maruyama, Mitsuru Shoji, Kenji Maeda, Naomi Kumahara, Shin Ichiro Tanaka, Masahiro Hirama

Research output: Contribution to journalArticle

38 Citations (Scopus)

Abstract

The extensive ring-expansion strategy for the synthesis of tetrahydrooxepin, oxocane, and hexahydrooxonin, which correspond to the D(E), I and F rings of ciguatoxin (CTX1B, 1). respectively, has been established. Chemoenzymatic acylation of the meso alcohols using a lipase provides an expeditious entry for the enantiomeric building blocks.

Original languageEnglish
Pages (from-to)7471-7498
Number of pages28
JournalTetrahedron
Volume55
Issue number24
DOIs
Publication statusPublished - Jun 11 1999

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Ciguatoxins
Acylation
Ethers
Lipase
Alcohols

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Enantioselective synthesis of the medium ring ethers, tetrahydrooxepin, oxocane and hexahydrooxonin, of ciguatoxin. Extensive ring-expansion and chemoenzymatic desymmetrization strategy. / Oishi, Tohru; Maruyama, Megumi; Shoji, Mitsuru; Maeda, Kenji; Kumahara, Naomi; Tanaka, Shin Ichiro; Hirama, Masahiro.

In: Tetrahedron, Vol. 55, No. 24, 11.06.1999, p. 7471-7498.

Research output: Contribution to journalArticle

Oishi, Tohru ; Maruyama, Megumi ; Shoji, Mitsuru ; Maeda, Kenji ; Kumahara, Naomi ; Tanaka, Shin Ichiro ; Hirama, Masahiro. / Enantioselective synthesis of the medium ring ethers, tetrahydrooxepin, oxocane and hexahydrooxonin, of ciguatoxin. Extensive ring-expansion and chemoenzymatic desymmetrization strategy. In: Tetrahedron. 1999 ; Vol. 55, No. 24. pp. 7471-7498.
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AU - Hirama, Masahiro

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