Stereocontrolled total synthesis of (−)-aspidophytine |
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Authors: | Shinjiro SumiKoji Matsumoto Hidetoshi Tokuyama Tohru Fukuyama |
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Affiliation: | a Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan b PRESTO, JST, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan |
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Abstract: | The enantioselective stereocontrolled total synthesis of aspidophytine is described. The key indole intermediate was prepared by radical cyclization of 2-alkenylphenylisocyanide, followed by Sonogashira-coupling with a highly functionalized terminal acetylene. The 11-membered cyclic amine, a precursor for the formation of the aspidosperma skeleton, was synthesized using nitrobenzenesulfonamide chemistry. After construction of the pentacyclic skeleton, the lactone ring was formed to complete the total synthesis. |
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Keywords: | total synthesis aspidophytine indole aspidosperma alkaloid macrocycles |
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