Bioinspired Total Synthesis of the Dimeric Indole Alkaloid (+)‐Haplophytine by Direct Coupling and Late‐Stage Oxidative Rearrangement |
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| Authors: | Dr. Hitoshi Satoh Ken‐ichi Ojima Dr. Hirofumi Ueda Prof. Dr. Hidetoshi Tokuyama |
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| Affiliation: | Graduate School of Pharmaceutical Sciences, Tohoku University, Sendai, Japan |
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| Abstract: | A bioinspired convergent total synthesis of (+)‐haplophytine, a dimeric indole alkaloid with diazabicyclo[3.3.1]nonane and hexacyclic aspidosperma segments, is described. This synthesis involves the direct coupling of the two segments in a AgNTf2‐mediated Friedel–Crafts reaction and construction of the diazabicyclo[3.3.1]nonane skeleton through late‐stage chemoselective aerobic oxidation of the 1,2‐diaminoethene moiety and a sequential semipinacol‐type rearrangement. |
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| Keywords: | alkaloids Friedel– Crafts reaction oxidation rearrangement total synthesis |
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