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Communication | Special issue | Vol 62, No. 1, 2004, pp.173-177
Published online, 27th October, 2003
DOI: 10.3987/COM-03-S(P)32
Synthesis in the Plakortone Series: Plakortone E

Patricia Y. Hayes and William Kitching*

*Department of Chemistry, School of Molecular and Microbial Sciences, The University of Queensland, St. Lucia, Brisbane, Queensland 4072, Australia

Abstract

A Pd(II)-mediated hydroxycyclisation-carbonylation-lactonisation sequence has operated efficiently with racemic enediol (8) to furnish (four) separable diastereomers of the bicyclic lactone system assigned to the sponge-derived, bioactive plakortone E. All four are cis ring-fused, and one is identical, on the basis of 1H and 13C NMR spectroscopic comparisons, with plakortone E, thus confirming its constitution and relative stereochemistry about the bicyclic lactone core. This synthetic approach, when applied to stereoisomer (13), will establish the absolute stereochemistry of plakortone E, likely to be that shown for (14).