Asymmetric Total Synthesis of (+)-Winchinine B.

J Org Chem

State Key Laboratory of Applied Organic Chemistry, Department of Chemistry , Lanzhou University, Lanzhou 730000 , People's Republic of China.

Published: November 2019

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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http://dx.doi.org/10.1021/acs.joc.9b02462DOI Listing

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