A microwave-assisted stereoselective synthesis of polyandrocarpamines A and B

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Davis, Rohan A
Baron, Paul S
Neve, Juliette E
Cullinane, Carleen
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2009
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Abstract

A stereoselective synthesis of the marine natural products, polyandrocarpamines A and B, has been achieved using a high-yielding one-step aldol condensation reaction under microwave conditions. The structures of both synthetic compounds were confirmed following 1D and 2D NMR, UV, IR and MS spectral analysis, and by comparison with literature data. Both synthetic natural products were assigned Z geometry about their exocyclic double bond on the basis of 13C/1H long-range coupling constants, which were measured using a gHSQMBC experiment. Polyandrocarpamines A and B were evaluated for their cytotoxicity towards the tumour cell lines, MCF-7 (breast), H460 (lung) and SF268 (central nervous system). Polyandrocarpamine A displayed selective cytotoxicity towards the SF268 cell line with a GI50 value of 65 卮

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Tetrahedron Letters

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50

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8

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© 2009 Elsevier. This is the author-manuscript version of this paper. Reproduced in accordance with the copyright policy of the publisher. Please refer to the journal's website for access to the definitive, published version.

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Medicinal and biomolecular chemistry

Biologically active molecules

Organic chemistry

Organic chemical synthesis

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