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SummaryThe ability of Rhodococcus rhodochrous (NCIMB 9703) to catalyse the regio- and stereoselective hydroxylation of a range of benzyloxy-substituted heterocycles has been investigated. Incubation of 2-benzyloxytetrahydropyrans with resting cell suspensions of the organism yielded predominantly a mixture of 5-hydroxylated isomers in combined yields of up to 40%. Exposure of the corresponding 2-benzyloxytetrahydrofuran derivatives to the cell suspensions gave predominantly the 4-hydroxylated isomers in yields of up to 26%. Most interestingly, 2-(4-nitrobenzyloxy)tetrahydrofuran and 2-(4-nitrobenzyloxy)tetrahydropyran were transformed in high yields to the 4-hydroxylated and 5-hydroxylated products, respectively.

Biohydroxylations of Cbz-Protected Alkyl Substituted Piperidines by Beauveria bassiana ATCC 7159. -The results of the title transformations to compounds such as (II), (IV), (V), and (VII) are compared to the recent published experiments of the corresponding benzoylated piperidines. Mechanistical aspects are discussed in detail. -(AITKEN, S. J.; GROGAN, G.; CHOW, C. S.-Y.; TURNER, N. J.; FLITSCH, S. L.; J. Chem. Soc., Perkin Trans. 1 [old] (1998) 20, 3365-3370; Dep. Chem., Univ. Edinburgh, Edinburgh EH9 3JJ, UK; EN)