Microbial hydroxylation of (Z)-2-benzylidene-1-azabicyclo[2.2.2]octan-3-one

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 alpha-(5S)-(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 (5 beta)-hydroxy epimer 3 and the (5 alpha,7 alpha)-dihydroxy derivative 4 were also produced by whole cell biotransformations of 1. (C) 1999 Elsevier Science Ltd. All rights reserved.