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