AN UNUSUAL FLUORIDE-MEDIATED OXIDATION OF GITOXIN

Akito NAGATSU; Yukitaka NAKAMURA; Kouya TAKEMOTO; Shin-ichi NAGAI; Taisei UEDA; Keiichiro HATANO; Jinsaku SAKAKIBARA; Toshihiro HASHIMOTO; Yoshinori ASAKAWA

doi:10.1248/cpb.44.258

Akito NAGATSU, Yukitaka NAKAMURA, Kouya TAKEMOTO, Shin-ichi NAGAI, Taisei UEDA, Keiichiro HATANO, Jinsaku SAKAKIBARA, Toshihiro HASHIMOTO, Yoshinori ASAKAWA

Author information

Akito NAGATSU
Yukitaka NAKAMURA
Kouya TAKEMOTO
Shin-ichi NAGAI
Taisei UEDA
Keiichiro HATANO
Jinsaku SAKAKIBARA
Toshihiro HASHIMOTO
Yoshinori ASAKAWA
Author's Organization：
Faculty of Pharmaceutical Sciences, Nagoya City University
Faculty of Pharmaceutical Sciences, Nagoya City University
Faculty of Pharmaceutical Sciences, Nagoya City University
Faculty of Pharmaceutical Sciences, Nagoya City University
Faculty of Pharmaceutical Sciences, Nagoya City University
Faculty of Pharmaceutical Sciences, Nagoya City University
Faculty of Pharmaceutical Sciences, Nagoya City University
Faculty of Pharmaceutical Sciences, Tokushima Bunri University
Faculty of Pharmaceutical Sciences, Tokushima Bunri University

Keywords: gitoxin, α, β-unsaturated γ-lactone, oxidation, fluoride ion

JOURNAL FREE ACCESS

1996 Volume 44 Issue 1 Pages 258-260

DOI https://doi.org/10.1248/cpb.44.258

Details

Abstract

An unusual oxidative transformation of α, β-unsaturated γ-lactone of the cardenolide gitoxin (1a) by tetra-n-butylammonium fluoride (TBAF) is reported. The structure of the product (2a) was finally confirmed by an X-ray crystal structure analysis of its genin (2b). The oxidation proceeded also in the presence of CsF, and KF + 18-crown-6.

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