Oximation of 20-hydroxyecdysone oxo derivatives proceeds regio- and stereoselectively and provides (E)-configured oximes in quantitative yields. The Ni–Ra-catalyzed hydrogenation of the oximes affords novel α-aminoecdysteroids with the unchanged 14α-hydroxy-7-en-6-on native chromophore of ecdysteroids. The structures of synthesized compounds were confirmed by the means of homo- and heteronuclear one-dimensional and two-dimensional 1H and 13C NMR spectroscopy and X-ray crystallography.
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.
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