J. W. Wong, M. Burns
Nov 19, 1999
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Influential Citations
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Journal
Tetrahedron-asymmetry
Abstract
Abstract Microbial hydroxylation of ( Z )-2-benzylidene-1-azabicyclo[2.2.2]octan-3-one 1 by various species of fungi and actinomycetes occurred regio- and stereoselectively at the 5 position of the quinuclidinone moiety. Most of the organisms produced α-(5 S )-( Z )-2-benzylidene-5-hydroxy-1-azabicyclo[2.2.2]octan-3-one 2 as the major product with enantiomeric excesses ranging from 30% to 84%. The (5β)-hydroxy epimer 3 and the (5α,7α)-dihydroxy derivative 4 were also produced by whole cell biotransformations of 1 .