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Total synthesis of (+)-cylindricine C
Authors:Toshiharu Arai
Institution:School of Pharmacy, Tokyo University of Pharmacy and Life Science, Horinouchi, Hachioji, Tokyo 192-0392, Japan
Abstract:A stereoselective total synthesis of (+)-cylindricine C has been achieved starting with (S)-N-Boc-2-pyrrolidinone. The key elements of this synthesis involve the sequence of reactions including BF3-mediated addition of the allyl Grignard reagent to the cyclic imine, spirocyclization via enamine formation, and intramolecular Michael addition to form the tricyclic core.
Keywords:Cylindricine  Cyclic imine  Grignard reaction  Azaspirocyclization  Intramolecular Michael addition
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