A three component condensation of aromatic amine, aldehyde, and cyclopentadiene with subsequent N trifluoroacetylation leads to 4 and 4,8 substituted N trifluoroacetyl 3a,4,5,9b tetrahydro 3H cyclopenta[c]quinolines. Ozonation of the double bond in the latter produced the corresponding isomeric stable ozonides having (1R*,4S*,5aR*,6S*,11bR*) configuration and differing in inversion at the carboxamide nitrogen atom.
Ozonation of N acyl 4 phenyl 3a,4,5,9b tetrahydro 3H cyclopenta[c]quinoline gave stable ozonides: a conformationally mobile isomer with the pseudoequatorial N acyl group and a conformationally stable isomer with the pseudoaxial N trifluoroacetyl group.
Steroids
SteroidsU 0300 Transformation of 20-Hydroxyecdysone Acetonides into Podecdysone B. -Hydrogenation of 20-hydroxyecdysone acetonides over Pd/C yields 20,22-acetonide (III). The latter is transferred to podecdysone B (IV) and trienone (V). -(ODINOKOV, V. N.; GALYAUTDINOV, I. V.; NEDOPEKIN, D. V.; VES'KINA, N. A.; KHALILOV, L. M.; Russ. J. Org. Chem. 39 (2003) 7, 952-956; Inst. Petrochem. Catal., Bashkortostan Rep. Acad. Sci., Ufa 450075, Russia; Eng.) -D. Singer 28-192
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