First total synthesis of (+/-)-stemonamide and (+/-)-isostemonamide |
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Authors: | Kende A S Hernando J I Milbank J B |
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Affiliation: | Department of Chemistry, University of Rochester, Rochester, NY 14627, USA. kende@chem.rochester.edu |
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Abstract: | [structure: see text] The total synthesis of the tetracyclic alkaloids stemonamide (1) and isostemonamide (2) is presented. The key step is the reaction between a silyloxyfuran and an N-acyliminium ion. The second quaternary center is created by an intramolecular aldol spirocyclization. After 1,4-addition of an appropriate side chain, the methyl and double bond are installed by Mannich reaction. The seven-membered ring is closed by intramolecular nucleophilic displacement. |
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