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Erika A. Crane, Dr. Thomas P. Zabawa, Rebecca L. Farmer and Prof. Dr. Karl A. Scheidt Enantioselective Synthesis of (−)-Exiguolide by Iterative Stereoselective Dioxinone-Directed Prins Cyclizations Angewandte Chemie International Edition 50

Version of Record online: 17 AUG 2011 | DOI: 10.1002/anie.201102790

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Three become one: The title compound can be prepared in 26 steps by employing a unified Prins cyclization strategy to construct both tetrahydropyran rings (see scheme). The route combines two similar dioxinone fragments and one aldehyde component to generate the core structure. (−)-Exiguolide selectively inhibits the growth of A549 cancer cells at low concentrations; the triene side chain and the Z-enoate geometry are both necessary for this cytotoxicity.

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