The isolation and synthesis of polyandrocarpamines A and B. Two new 2-aminoimidazolone compounds from the Fijian ascidian, Polyandrocarpa sp.

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Title The isolation and synthesis of polyandrocarpamines A and B. Two new 2-aminoimidazolone compounds from the Fijian ascidian, Polyandrocarpa sp.
Author Davis, Rohan Andrew; Aalbersberg, William; Meo, Semisi; Rocha, Rosana Moreira da; Ireland, Chris M.
Journal Name Tetrahedron
Year Published 2002
Place of publication United Kingdom
Publisher Elsevier
Abstract Chem. investigation of a Fijian ascidian, Polyandrocarpa sp., has resulted in the isolation of two new 2-aminoimidazolone-derived compds., polyandrocarpamines A (I) and B (II). The structures of these unique metabolites were detd. by the interpretation of spectroscopic data and confirmed by total synthesis. The stereospecific synthesis of I was accomplished using aldol condensation chem. to generate an arylidene thiohydantoin that was subsequently transaminated to yield polyandrocarpamine A. Demethylation of synthetic I afforded polyandrocarpamine B. Both the natural product and synthetic polyandrocarpamines were assigned Z geometries about the exocyclic double bond (C-5/C-7) on the basis of 13C/1H long-range coupling consts., which were measured using a gHSQMBC expt.
Peer Reviewed Yes
Published Yes
Publisher URI http://www.sciencedirect.com/science/journal/00404020
Alternative URI http://dx.doi.org/10.1016/S0040-4020(02)00228-4
Copyright Statement Copyright 2002 Elsevier. Please refer to the journal's website for access to the definitive, published version. This is the author-manuscript version of this paper. Reproduced in accordance with the copyright policy of the publisher. "
Volume 58
Issue Number 16
Page from 3263
Page to 3269
ISSN 0040-4020
Date Accessioned 2006-07-28
Date Available 2009-09-10T05:13:18Z
Language en_AU
Research Centre Eskitis Institute for Drug Discovery
Faculty Eskitis, Inst Cell&Molecular Therapies
Subject PRE2009-Organic Chemistry
URI http://hdl.handle.net/10072/16734
Publication Type Journal Articles (Refereed Article)
Publication Type Code c1x

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