A microwave-assisted stereoselective synthesis of polyandrocarpamines A and B

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 1 D 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 (13)C/(1)H 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 GI(50) value of 65 mu M. (C) 2008 Elsevier Ltd. All rights reserved.