Stereochemistry of ethynylation, normant, and grignard reactions in the 1-alkyldecahydro-4-quinolone series

The different stereochemistries of the addition of acetylene and vinyl- or ethylmagnesium bromides to 1-alkyl- and 1,2,2-trimethyl-trans-decahydro-4-quinolones are shown. In the ethynylation of mixtures of cis- and trans-1-alkyldecahydro-4-quinolones, one acetylenic alcohol of the cis series was isolated in each case in addition to two epimeric (with respect to the 4 position) trans alcohols. The configurations of the synthesized alcohols were established by IR spectroscopy.