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Concise syntheses of the natural products cavicularin (ten steps) and riccardin C (seven steps) are reported. Key features of the new synthetic route are a convergent strategy to assemble acyclic precursors and a sequence of regioselective reduction and halogenation steps to facilitate Wittig macrocyclisation and transannular ring contraction reactions. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Citation

Sarah L Kostiuk, Timothy Woodcock, Leo F Dudin, Peter D Howes, David C Harrowven. Unified syntheses of cavicularin and riccardin C: addressing the synthesis of an arene adopting a boat configuration. Chemistry (Weinheim an der Bergstrasse, Germany). 2011 Sep 19;17(39):10906-15

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PMID: 21932232

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