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

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.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 345–348, March, 1994.