Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 22, Pages 14994-15000Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b02462
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Funding
- National Science Foundation of China [21732001, 21871118, 21572088]
- PCSIRT [IRT_15R28]
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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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