Eudistomidin G, a new b-carboline alkaloid from the Okinawan marine tunicate Eudistoma glaucus and structure revision of eudistomidin B

A new b-carboline alkaloid, eudistomidin G ( 1), has been isolated from the Okinawan marine tunicate Eudistoma glaucus, and the structure was elucidated from spectroscopic data. Furthermore, the structure of eudistomidin B ( 2), which has been isolated from the same tunicate, was revised from 2a to...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2010-07, Vol.20 (14), p.4100-4103
Main Authors: Takahashi, Yohei, Ishiyama, Haruaki, Kubota, Takaaki, Kobayashi, Jun'ichi
Format: Article
Language:English
Subjects:
Eudistoma
Glaucus
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Summary:A new b-carboline alkaloid, eudistomidin G ( 1), has been isolated from the Okinawan marine tunicate Eudistoma glaucus, and the structure was elucidated from spectroscopic data. Furthermore, the structure of eudistomidin B ( 2), which has been isolated from the same tunicate, was revised from 2a to 2b by detailed analyses of spectroscopic data. Asymmetric synthesis of the revised structure ( 2b) of eudistomidin B ( 2) and its (1S,10S)-diastereomer ( 2c) has been accomplished with the Noyori catalytic asymmetric hydrogen-transfer reaction. The absolute configuration of eudistomidin B ( 2) was confirmed to be 2b possessing (1R,10S)-configuration, from comparison of the super(1)H NMR data, CD spectra, [a] sub(D) values, and HPLC analysis of 2b, 2c, and natural eudistomidin B.
ISSN:0960-894X
DOI:10.1016/j.bmcl.2010.05.071