Alcohol Dehydrogenase?triggered Oxa?Michael Reaction for the Asymmetric Synthesis of Disubstituted Tetrahydropyrans and Tetrahydrofurans

© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim An alcohol dehydrogenase-mediated asymmetric reduction and subsequent intramolecular oxa-Michael reaction has been developed for the preparation of tetrahydropyrans (or oxanes) and tetrahydrofurans, in excellent conversion, yield and high enantiomeric and diastereomeric excess. To highlight the utility of the methodology, we report the synthesis of an analogue of the fungal antioxidant brocaketone A. Also described is the preparation of the (–)-(R,R)-enantiomer of the natural product, (+)-(S,S)-(cis-6-methyltetrahydropyran-2-yl)acetic acid