BIOHYDROXYLATIONS OF CBZ-PROTECTED ALKYL SUBSTITUTED PIPERIDINES BY BEAUVERIA-BASSIANA ATCC-7159

Citation
Sj. Aitken et al., BIOHYDROXYLATIONS OF CBZ-PROTECTED ALKYL SUBSTITUTED PIPERIDINES BY BEAUVERIA-BASSIANA ATCC-7159, Journal of the Chemical Society. Perkin transactions. I (Print), (20), 1998, pp. 3365-3370
Citations number
31
Categorie Soggetti
Chemistry Inorganic & Nuclear
ISSN journal
0300922X
Issue
20
Year of publication
1998
Pages
3365 - 3370
Database
ISI
SICI code
0300-922X(1998):20<3365:BOCASP>2.0.ZU;2-U
Abstract
N-Benzyloxycarbonyl (Cbz) protected piperidines are hydroxylated with greater regioselectivity than the corresponding N-benzoyl analogues wh en incubated with the fungus Beauveria bassiana ATCC 7159. Cbz-protect ed piperidines 1-3, 5-7, have been biotransformed by growing cell susp ensions of this fungus to yield predominantly 4-hydroxylated products in up to 48% yield. The regiospecificity of hydroxylation was only com promised significantly with N-Cbz-3-methylpiperidine 3 and N-Cbz-2-met hylpiperidine 4 where hydroxylation occurred in both the 3 and 4 posit ions.