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Synthesis of the Tetracyclic Core of the Daphlongeranines
Benjamin D A Shennan1, Peter W Smith1, Yusuke Ogura1
1Department of Chemistry, University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford OX1 3TA, U.K.
Abstract:
The first synthesis of the tetracyclic core of the daphlongeranine natural product family is reported. Containing a tricyclic core unique to this subfamily of the Daphniphyllum alkaloids and featuring two quaternary carbons, this 11-step synthetic route featured the application of a three-step spirocyclization strategy and development of a new intramolecular Pd-catalyzed cyclization reaction. Additionally, the route included the application of an XAT-initiated Giese addition and demonstration of an enantioselective synthesis of the bicyclic core.
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