A novel total synthesis of the bioactive poly-substituted carbazole alkaloid carbazomadurin A |
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Authors: | Yuhzo Hieda Sayuri Kishida |
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Institution: | Graduate School of Pharmacy & Pharmaceutical Sciences, and Faculty of Pharmacy & Pharmaceutical Sciences, Fukuyama University, Fukuyama, Hiroshima 729-0292, Japan |
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Abstract: | A new total synthesis of the neuronal cell-protecting carbazole alkaloid carbazomadurin A is described. The key step was an allene-mediated electrocyclic reaction involving an indole b]-bond for the construction of a highly substituted carbazole ring. The E-alkenyl side chain at the C1 position of carbazole was introduced between O-triflate and alkenyl pinacol borate using the Suzuki-Miyaura reaction. SEM groups were cleaved with TBAF and the formyl group was reduced to provide carbazomadurin A. |
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Keywords: | Carbazomadurin A Carbazole Allene-mediated electrocyclic reaction Total synthesis |
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