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Asymmetric Total Synthesis of Vincadifformine Enabled by a Thiourea‐Phosphonium Salt Catalyzed Mannich‐Type Reaction
Author(s) -
Pan Lu,
Zheng ChangWu,
Fang GuoSheng,
Hong HaoRan,
Liu Jun,
Yu LongHui,
Zhao Gang
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201900896
Subject(s) - thiourea , phosphonium salt , chemistry , phosphonium , trifluoroacetic acid , total synthesis , salt (chemistry) , mannich reaction , catalysis , phosphine , combinatorial chemistry , organocatalysis , organic chemistry , enantioselective synthesis
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.