Extensive Ring-Expansion Strategy for the Enantioselective Synthesis of the Medium Ring Ethers, Oxepene, Oxocane, and Oxonene, of Ciguatoxin

Tohru Oishi, Mitsuru Shoji, Kenji Maeda, Naomi Kumahara, Masahiro Hirama

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

The extensive ring-expansion strategy for the synthesis of oxepene 19, oxocane 23, and oxonene 28, which correspond to the D (E), I and F ring fragments of ciguatoxin (1), respectively, has been established. Chemoenzymatic asymmetric acylation of the meso alcohols using lipase AK provided a simple entry of the enantiomeric building blocks.

Original languageEnglish
Pages (from-to)1165-1167
Number of pages3
JournalSynlett
Volume1996
Issue number12
Publication statusPublished - 1996
Externally publishedYes

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Oxepins
Ciguatoxins
Acylation
Ethers
Lipase
Alcohols

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Extensive Ring-Expansion Strategy for the Enantioselective Synthesis of the Medium Ring Ethers, Oxepene, Oxocane, and Oxonene, of Ciguatoxin. / Oishi, Tohru; Shoji, Mitsuru; Maeda, Kenji; Kumahara, Naomi; Hirama, Masahiro.

In: Synlett, Vol. 1996, No. 12, 1996, p. 1165-1167.

Research output: Contribution to journalArticle

Oishi, T, Shoji, M, Maeda, K, Kumahara, N & Hirama, M 1996, 'Extensive Ring-Expansion Strategy for the Enantioselective Synthesis of the Medium Ring Ethers, Oxepene, Oxocane, and Oxonene, of Ciguatoxin', Synlett, vol. 1996, no. 12, pp. 1165-1167.
Oishi, Tohru ; Shoji, Mitsuru ; Maeda, Kenji ; Kumahara, Naomi ; Hirama, Masahiro. / Extensive Ring-Expansion Strategy for the Enantioselective Synthesis of the Medium Ring Ethers, Oxepene, Oxocane, and Oxonene, of Ciguatoxin. In: Synlett. 1996 ; Vol. 1996, No. 12. pp. 1165-1167.
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