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6,11-Dioxa-D-homoanalogs of steroids by reaction of 2-acetyl-2-cyclohexen-1-ones with 4-hydroxycoumarins

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Unsubstituted 2-acetyl-2-cyclohexetz-1-one reacts with 4-hydroxycoumarin following the pattern of a Diels -Alder heterodiene condensation to form 12-methyl-6,11-dioxa-9-hydroxy-D-homo-1,3,5(10), 12-tetraene-7,17a-dione. In the case of 2-acetyl-5,5-dimethyl-2-cyclohexen-1-one, reaction with both 4-hydroxy- and 4,7-dihydroxycoumarin follows the pattern of a Michael addition with the formation of 3-(2-acetyl-5,5-dimethyl-3-oxocyclohexyl)-4-hydroxy-and 4,7-dihydroxy coumarin respectively. Dehydration of both types of adduct gives 6,11-dioxa-D-homoanalogs of steroids.

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Authors and Affiliations

  1. Institute of Bioorganic Chemistry, Belarus Academy of Sciences, 220141, Minsk

    A. N. Pyrko

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  1. A. N. Pyrko
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 345–348, March, 1994.

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Pyrko, A.N. 6,11-Dioxa-D-homoanalogs of steroids by reaction of 2-acetyl-2-cyclohexen-1-ones with 4-hydroxycoumarins. Chem Heterocycl Compd 30, 305–307 (1994). https://doi.org/10.1007/BF01165695

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  • DOI: https://doi.org/10.1007/BF01165695

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