Total Synthesis of Indole Alkaloid Alsmaphorazine D |
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Authors: | Chenlong Zhu Zhaobo Liu Guanyu Chen Kai Zhang Prof?Dr Hanfeng Ding |
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Institution: | Department of Chemistry, Zhejiang University, 148 Tianmushan Road, Hangzhou 310028 (China) |
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Abstract: | A concise total synthesis of rac‐alsmaphorazine D has been described for the first time. The efficient synthetic strategy features four key transformations: 1) a catalytic intramolecular oxidative cyclization for the δ‐lactamindole backbone; 2) an oxidative cyclic aminal formation for the hexahydropyrrolo2,3‐b]pyrrole framework; 3) a transannular radical cyclization for the construction of the diazabicyclo3.3.1]nonane structure; and 4) a one‐pot desilylation/double epimerization reaction that affirms the relative stereochemistry. |
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Keywords: | cyclization epimerization oxidative coupling pyrroloindoles total synthesis |
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