Stereochemistry of ethynylation of 2,7-dialkyl- and 1,2,7-trialkyl-trans-decahydro-4-quinolones

The effect of the nature of the acetylide, the temperature, and the character of the solvent on the stereochemistry of ethynylation of isomeric 2,7-dialkyl- and 1,2,7-trialkyldecahydro-4-quinolones was investigated. Acetylenic alcohols that have an axially oriented ethynyl grouping were synthesized. Conditions for the stereospecific synthesis of epimeric (with respect to C₄) acetylenlc alcohols were found. The isomers of acetylenic alcohols obtained were incapable of interconversions under the reaction conditions.See 1] for our preliminary communication.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1086–1091, August, 1980.