State Key Laboratory of Applied Organic Chemistry, Department of Chemistry , Lanzhou University , Lanzhou 730000 , People's Republic of China.
J Org Chem. 2019 Nov 15;84(22):14994-15000. doi: 10.1021/acs.joc.9b02462. Epub 2019 Nov 7.
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.
从商业可得的原料出发，经 12 步反应，首次实现了阿朴菲类生物碱(+)-卫矛宁 B 的不对称全合成。采用了一种新的合成策略，其中包括高效的氮杂迈克尔加成、钌催化的转移脱氢以及分子内钯催化的氧化偶联，以构建 ABC 三环体系。我们小组开发的一锅法反应，包括羰基还原/亚胺形成/分子内共轭加成，用于构建 D 环部分。
