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Asymmetric Total Synthesis of Vincadifformine Enabled by a Thiourea-Phosphonium Salt Catalyzed Mannich-Type Reaction
Lu Pan1, Chang-Wu Zheng1, Guo-Sheng Fang1
1Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. China.
Abstract:
An asymmetric total synthesis of vincadifformine is described. The limited tactics with chiral cation-directed catalysis in total synthesis inspired the development of our strategy for accessing this alkaloid in enantionrich form. The route features a thiourea-phosphonium salt catalyzed Mannich-type reaction, a phosphine-promoted aza-Morita-Baylis-Hillman reaction and a trifluoroacetic acid promoted deprotection/amidation cascade process.
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