Alcohol Dehydrogenase-triggered Oxa-Michael Reaction for the Asymmetric Synthesis of Disubstituted Tetrahydropyrans and Tetrahydrofurans
Alcohol Dehydrogenase-triggered Oxa-Michael Reaction for the Asymmetric Synthesis of Disubstituted Tetrahydropyrans and Tetrahydrofurans
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DOI：
10.1002/cctc.201900658
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发表时间：
2019-07-09
期刊：
影响因子：
4.5
通讯作者：
O'Reilly, Elaine
中科院分区：
文献类型：
--
作者：
Eastman, Harry;Ryan, James;O'Reilly, Elaine
本文报道了一种醇脱氢酶介导的不对称还原和随后的分子内oxa-Michael反应，用于制备四氢吡喃（或oxanes）和四氢呋喃，具有良好的转化率、产率和高的对映体和非对映体过量。为了突出该方法的实用性，我们报告了真菌抗氧化剂溴酮A的类似物的合成。还描述了天然产物（+）-（S，S）-（顺式-6-甲基四氢吡喃-2-基）乙酸的（-）-（R，R）-对映体的制备。
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.