Total Synthesis of (+)??Aquaticol by Biomimetic Phenol Dearomatization: Double Diastereofacial Differentiation in the Diels–Alder Dimerization of Orthoquinols with a …

J Gagnepain, F Castet…

Index: Gagnepain, Julien; Castet, Frederic; Quideau, Stephane Angewandte Chemie - International Edition, 2007 , vol. 46, # 9 p. 1533 - 1535

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Citation Number: 75

Abstract

(+)-Aquaticol (1a) is a bissesquiterpene that was isolated from Veronica anagallis-aquatica, a plant used in traditional Chinese medicine.[1] Retrosynthetic analysis of its structure quickly revealed that it should be accessible through a Diels–Alder dimerization of the orthoquinol (6R, 7S)-2,[2] which could itself be derived from natural (À)-hydroxycuparene ((À)-3) by hydroxylation accompanied by dearomatization (Scheme 1).[3] Although ...