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

doi:10.1055/s-1996-5729

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 journal › Article › peer-review

45 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 language	English
Pages (from-to)	1165-1167
Number of pages	3
Journal	Synlett
Volume	1996
Issue number	12
DOIs	https://doi.org/10.1055/s-1996-5729
Publication status	Published - Jan 1 1996
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1055/s-1996-5729

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AU - Maeda, Kenji

AU - Kumahara, Naomi

AU - Hirama, Masahiro

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

Abstract

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