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Issue 20, 2000
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Total synthesis of (−)-eudistomins with an oxathiazepine ring. Part 1. Formation of the oxathiazepine ring system

Masako Nakagawa,*a  Jin-Jun Liu,a  Tohru Hino,a  Akihiko Tsuruoka,a  Naoyuki Harada,a  Makoto Arigaa  and  Yasunori Asadaa 
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* Corresponding authors

a Faculty of Pharmaceutical Sciences, Chiba University, Yayoi-cho, Chiba-shi, Japan

Abstract

Formation of the oxathiazepine ring in eudistomins 1 was investigated. Thiazolidinyl-β-carboline 5 was successfully transformed into thiaindoloquinolizidine 7, but attempted oxidative transformation of 7 to 1 was not successful. The oxidative cyclization of 1-substituted-2 hydroxy-β-carboline 24 with NCS or the acid-catalyzed cyclization of the corresponding S-oxide 26 with TsOH gave oxathiazepine 25, which was readily converted to (+)-debromoeudistomin L (+)-1f. (−)-Debromoeudistomin L (−)-1f was prepared from N-hydroxytryptamine 11 and the D-cysteinal 30.

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Publication details

The article was received on 01 Jun 2000, accepted on 11 Aug 2000 and first published on 27 Sep 2000


Article type: Paper
DOI: 10.1039/B004570P
Citation: J. Chem. Soc., Perkin Trans. 1, 2000,0, 3477-3486
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    Total synthesis of (−)-eudistomins with an oxathiazepine ring. Part 1. Formation of the oxathiazepine ring system

    M. Nakagawa, J. Liu, T. Hino, A. Tsuruoka, N. Harada, M. Ariga and Y. Asada, J. Chem. Soc., Perkin Trans. 1, 2000, 0, 3477
    DOI: 10.1039/B004570P

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