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Communication | Regular issue | Vol 6, No. 8, 1977, pp.1105-1112
Published online, 1st January, 1970
DOI: 10.3987/R-1977-08-1105
A Stereoelectronic Requirement for the Cyclization of cis- and trans-N-Acrylyloctahydro-7(1H)-quinolones to Decahydro-3H,10H-benzo[i,j]quinolizine-3,10-diones

Takefumi Momose,* Shuji Uchida, Takeshi Imanishi, San-Wong Kim, Nobuko Takahashi, and Sen-ichi Horii

*Faculty of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Toyonaka, Osaka 560-0043, Japan


Cyclization of N-acrylyl-cis- and -trans-octahydro-7(1H)-quinolones to decahydro-3H,10H-benzo[i,j]quinolizine-3,10-diones is described. Possible stereoelectronic control in the intramolecular Michael addition step of cyclization, or a requirement for the successful ring closure, was discussed on the basis of experiments using stereoisomers of the model compounds.