Abstract
Acid-catalyzed three-component condensation of methyl 12-aminodehydroabietate, aromatic aldehydes, and cyclopentadiene gave methyl (4R)-4-aryl-6-isopropyl-10,13a-dimethyl-3a,4,5,8,9,9a,10,11,12,13,13a,13d-dodecahydro-3H-cyclopenta[c]naphtho[1,2-f]quinoline-10-carboxylates and their (4S)-diastereomers. Ozonolysis of the double bond in their N-trifluoroacetyl derivatives synthesized from the (4R)-diastereomers afforded the corresponding ozonides with the (1S,4R,5aS,6R,11aR,12R,15aS,15dR)-configuration.
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