TRANSFORMATION OF 1,2,5,6-TETRAHYDROPYRIDINES WITH MYCELLAR FUNGI

Authors

  • П. Б. Терентьев Moscow M. V. Lomonosov State University, Moscow 119234
  • Т. М. Зильберштейн Moscow M. V. Lomonosov State University, Moscow 119234
  • А. А. Борисенко Moscow M. V. Lomonosov State University, Moscow 119234
  • В. А. Шморгунов Moscow M. V. Lomonosov State University, Moscow 119234
  • Н. Ф. Пискункова Moscow M. V. Lomonosov State University, Moscow 119234
  • Г. В. Гришина Moscow M. V. Lomonosov State University, Moscow 119234

Keywords:

piperidinediol, 1,2,5,6-tetrahydropyridine, mycellar fungi, biotransformation, hydroxylation

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.

How to Cite
Terentiev, P. B.; Zilberstein, T. M.; Borisenko, A. A.; Shmorgunov, V. A.; Piskunkova, N. F.; Grishina, G. V. Chem. Heterocycl. Compd. 2003, 39, 885. [Khim. Geterotsikl. Soedin. 2003, 1027.]

For this article in the English edition, see DOI https://doi.org/10.1023/A:1026142220384

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Published

2003-07-25

Issue

No. 7 (2003)

Section

Original Papers