Journal
TETRAHEDRON
Volume 66, Issue 35, Pages 7083-7087Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.07.013
Keywords
DHMEQ; Asymmetric epoxidation; Lipase; Hydrolysis; Kinetic resolution
Categories
Funding
- Ministry of Education, Culture, Sports, Science and Technology, Japan
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A new route for (2S,3S,4S)-form, the physiologically active stereoisomer of dehydroxymethylepoxyquinomicin (DHMEQ), a potent NF-kappa B inhibitor, was established by chemoenzymatic approach. Elaboration on the asymmetric epoxidation of a p-benzoquinone monoketal with benzylcinchonidinium tert-butylhydroperoxide yielded an epoxyenone, in 79.8% ee and 57% yield in reproducible manner. By way of the transformation of this key intermediate to enantiomerically pure (2S,35,4S)-DHMEQ the contaminating undesired enantiomer could be effectively removed by applying Burkholderia cepacia lipase-catalyzed hydrolysis of diacylated precursor. The above integrated combination of chemical asymmetric synthesis and enzyme-catalyzed kinetic resolution enabled us to prepare active DHMEQ in a large-scale. (C) 2010 Elsevier Ltd. All rights reserved.
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