Stereoselective nitrenium ion cyclizations: asymmetric synthesis of the (+)-Kishi lactam and an intermediate for the preparation of fasicularin |
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| Authors: | Duncan J. Wardrop Wenming Zhang Chad L. Landrie |
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| Affiliation: | Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607-7061, USA |
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| Abstract: | The asymmetric synthesis of the (+)-Kishi lactam and an intermediate for the preparation of the marine natural product fasicularin is reported. The keystone of this divergent synthesis is the diastereoselective azaspirocyclization of an N-methoxy γ-arylbutanoamide, which is believed to proceed through the intermediacy of an N-acylnitrenium ion. |
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| Keywords: | Nitrenium ions Dearomatization Fasicularin Polyvalent iodine Histrionicotoxin |
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