Stereodivergent process for the synthesis of the decahydroquinoline type of dendrobatid alkaloids.
A flexible and stereodivergent synthesis of the cis- and trans-fused 2,5-disubstituted octahydroquinolinone ring systems bearing all four stereogenic centers for the synthesis of the decahydroquinoline type of dendrobatid alkaloids has been achieved. The strategy involves stereoselective and stereodivergent construction of 2,3,6-trisubstituted piperidine ring systems using the Michael type of conjugate addition reaction to the enaminoesters 1 and 3, the intramolecular aldol type of cyclization reaction of keto aldehydes 11 and 12, and ring-closing metathesis of 21 as key steps.
Toyooka
Naoki
N
Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, Sugitani 2630, Toyama 930-0194, Japan. toyooka@ms.toyama-mpu.ac.jp
Okumura
Maiko
M
Nemoto
Hideo
H
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D008968:Molecular Conformation; D015394:Molecular Structure; D015363:Quinolones / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D015363:Quinolones