rac-9-ethyl-12a-hydroxytetradecahydrotriphenylene-1,5(2H,4bH)-dione: stabilization of a new isomer of a functionalized perhydrotriphenylene through a tandem Michael addition-aldol reaction.
The title compound, C20H30O3, is a new functionalized perhydrotriphenylene derivative formed via a tandem Michael addition-aldol reaction. The structural study reveals that the system of fused rings approximates a C2 point symmetry, with trans-cis-cis ring junctions, while highly symmetric all-trans perhydrotriphenylene, previously characterized, approximates a D3 symmetry. The perhydrotriphenylene nucleus of the title compound corresponds to the third stable stereoisomer isolated for this polycyclic system. Considering that the C(s) isomer was obtained recently through a similar tandem reaction, a general strategy is proposed which may help to obtain other stable stereoisomers of perhydrotriphenylene.
Universidad de las Américas Puebla, Departamento de Ciencias Químico-Biológicas, Santa Catarina Mártir S/N, Cholula, 72820 Puebla, Mexico.
Luis Arturo
LA
García
Sylvain
S
Bernès
Cecilia
C
Anaya de Parrodi