Journal of Organic Chemistry p. 14994 - 15000 (2019)
Update date:2022-08-10
Topics:
Liu, Zaimin
Ju, Xiaolin
Ma, Shiqiang
Du, Chenglong
Zhang, Weiwei
Li, Huilin
Wang, Xiaolei
Xie, Xingang
She, Xuegong
The first asymmetric total synthesis of aspidosperma alkaloid (+)-winchinine B was achieved in 12 steps from commercially available materials. A new synthetic strategy which features an efficient aza-Michael addition, a ruthenium-catalyzed transfer dehydrogenation, and an intramolecular palladium-catalyzed oxidative coupling was adopted to install the ABC tricycle system. A one-pot process involving carbonyl reduction/iminium formation/intramolecular conjugate addition developed by our group was utilized to construct the D ring moiety.
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