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Stereochemistry of nitrogenous heterocycles. 61. Synthesis and configuration of an eighth isomer of 2-methyl-4-hydroxydecahydroquinoline

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Abstract

Reduction of 1-benzoyl-2α-methyl-4-oxo-cis-decahydroquinoline with sodium borohydride and sodium in alcohol has given 1-benzoyl-2α-methyl-4Β-hydroxy-cis-decahydroquinoline, which exists in the steroidal conformation with diaxial α, α′-substituents in the piperidine ring and with an equatorial hydroxy-group. Debenzoylation of this has given the last of the eight theoretically possible isomers of 2-methyl-4-hydroxydecahydroquinoline, namely 2α-methyl-4Β-hydroxy-cis-decahydroquinoline, which exists in the nonsteroidal conformation with an axial hydroxy-group.

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Authors and Affiliations

  1. Institute of Chemical Sciences, Academy of Sciences of the Kazakh SSR, 480100, Alma-Ata

    G. S. Litvinenko & L. A. Voronenko

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  1. G. S. Litvinenko
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  2. L. A. Voronenko
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Additional information

For communication 60, see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 238–243, February, 1987.

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Litvinenko, G.S., Voronenko, L.A. Stereochemistry of nitrogenous heterocycles. 61. Synthesis and configuration of an eighth isomer of 2-methyl-4-hydroxydecahydroquinoline. Chem Heterocycl Compd 23, 200–204 (1987). https://doi.org/10.1007/BF00663862

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  • DOI: https://doi.org/10.1007/BF00663862

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