Total synthesis of tryprostatins A and B |
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Authors: | Takayuki YamakawaEiji Ideue Yuzo IwakiAyumu Sato Hidetoshi TokuyamaJun Shimokawa Tohru Fukuyama |
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Institution: | a Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan b Graduate School of Pharmaceutical Sciences, Tohoku University, Sendai 985-8578, Japan |
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Abstract: | Three distinct synthetic routes to the 2-prenyl tryptophan core skeleton of tryprostatins and their total syntheses are described. The strategies include a traditional gramine-mediated coupling reaction, Fürstner indole synthesis, and our radical-mediated indole synthesis from o-alkenylphenyl isocyanide. The establishment of reliable conditions for the radical-mediated construction of indoles via a low-temperature radical initiator V-70 (2,2′-azobis(4-methoxy-2,4-dimethylvaleronitrile)) led to the highly efficient syntheses of tryprostatins A and B. |
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Keywords: | Total Synthesis Natural product Radical cyclization Alkaloids |
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