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Stereoselective acetylation of 3,4-dihydro-3,4-dihydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

✍ Scribed by Ramesh N. Patel; Amit Banerjee; Clyde G. McNamee; Laszlo J. Szarka

Publisher: Elsevier Science
Year: 1995
Tongue: English
Weight: 351 KB
Volume: 6
Category: Article
ISSN: 0957-4166
DOI: 10.1016/0957-4166(94)00367-k

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✦ Synopsis

The chiral intermediate diol (3S,4R)-trans-3,4-dihydro-3,4-dihydroxy-2,2dimethyl-2H-1-benzopyran-6-carbonitrile 2. was prepared for the total synthesis of a potassium channel opener drug candidate. The stereoselective acetylation of racemic lwas carded out with various lipases among which the lipases from Candida cylindraceae and Pseudomonas cepacia catalyzed the acetylation of the undesired enantiomer of racemic 1 to yield monoacetylated product and unreacted desired (+)-trans diol 2. A reaction yield of >40% and an optical purity >90% were obtained using each lipase.

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