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

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Davis, RA
Aalbersberg, W
Meo, S
da Rocha, RM
Ireland, CM
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2002
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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.

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Tetrahedron

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58

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16

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© 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. "

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Medicinal and biomolecular chemistry

Organic chemistry

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