期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 57, 期 46, 页码 15232-15236出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201809678
关键词
Alkaloids; cyclization; isocyanides; natural product synthesis; spiroindolines
资金
- Hercules Foundation [AUGE/11/029]
- Netherlands Organisation for Scientific Research (NWO)
The N-iodosuccinimide-mediated spirocyclization of tryptamine-derived isocyanides to generate spiroindolenines is reported. The products contain both an imine and an imidoyl iodide as flexible handles for follow-up chemistry. Nucleophilic addition typically occurs chemoselectively on the imine moiety with complete diastereoselectivity, providing opportunities for the construction of complex molecular frameworks. The synthetic potential of the method was showcased in the formal total synthesis of (+/-)-aspidofractinine.
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