Abstract
It has been shown that on biotransformation of a series of 1,2,5,6-tetrahydropyridines with strains of the mycellar fungi Cunninghamella verticillata VKPM F-430, Beauveria bassiana ATCC 7159, and Penicillium simplicissimum KM-16, the culture of Cunninghamella verticillata possesses the greatest transforming activity and selectivity. With the aid of the latter practically quantitative oxidation of 1,2,5,6-tetrahydropyridines occurs into the corresponding trans-diol. The structure and spatial disposition of trans-1-benzyl-3,4-dihydroxypiperidine was demonstrated by data of chromato-mass spectrometric analysis and high resolution NMR spectra and was confirmed by comparison with an authentic sample obtained by an alternate synthesis using the oxidation of 1-benzyl-1,2,5,6-tetrahydropyridine with trifluoroperacetic acid.
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Terentiev, P.B., Zilberstein, T.M., Borisenko, A.A. et al. Transformation of 1,2,5,6-Tetrahydropyridines with Mycellar Fungi. Chemistry of Heterocyclic Compounds 39, 885–894 (2003). https://doi.org/10.1023/A:1026142220384
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DOI: https://doi.org/10.1023/A:1026142220384