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

Abstract

Unsubstituted 2-acetyl-2-cyclohexen-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.

How to Cite
Pyrko, A. N. Chem. Heterocycl. Compd. 1994, 30, 305. [Khim. Geterotsikl. Soedin. 1994, 345.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF01165695