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ORGANIC LETTERS
卷 25, 期 27, 页码 5044-5048出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.3c01740
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We report a concise approach to the synthesis of phenanthroindolizidine alkaloids, utilizing the interception of strained azacyclic alkynes in Pd-catalyzed reactions. Two types of strained intermediates, a functionalized piperidyne and a new strained intermediate, indolizidyne, were evaluated. These efforts resulted in the successful synthesis of three natural products: tylophorine, tylocrebine, and isotylocrebine, demonstrating the successful combination of strained azacyclic alkyne chemistry with transition-metal catalysis for the construction of complex heterocycles.
Wereport a concise approach to phenanthroindolizidine alkaloids,wherein strained azacyclic alkynes are intercepted in Pd-catalyzedannulations. Two types of strained intermediates were evaluated: afunctionalized piperidyne and a new strained intermediate, an indolizidyne.We show that each can be employed, ultimately allowing access to threenatural products: tylophorine, tylocrebine, and isotylocrebine. Theseefforts demonstrate the successful merger of strained azacyclic alkynechemistry with transition-metal catalysis for the construction ofcomplex heterocycles.
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