Total Synthesis of Cristatic Acid Based on Late??Stage Decarboxylative Allylic Migration and Biomimetic Aromatization of a Diketo Dioxinone

NS George, KE Anderson…

Index: George, Nicolas S.; Anderson, Katie E.; Barrett, Anthony G. M. European Journal of Organic Chemistry, 2013 , # 33 p. 7604 - 7610

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Citation Number: 5

Abstract

Abstract A fifteen-step synthesis of methyl cristatate is described. tert-Butyl-[(E)-6-iodo-3- methylhex-2-enyloxy)] diphenylsilane, synthesized from geraniol, was coupled with 2- (diethoxymethyl)-4-lithiofuran and transformed–by acetal hydrolysis, Wittig olefination, and desilylation–into a sesquiterpene furan alcohol. This alcohol was converted into methyl cristatate by sequential condensation with carbonyldiimidazole and the enolate dianion ...

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