Total Synthesis of the Proposed Structure of Neaumycin B |
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| Authors: | Sen Zhang Songming Zhang Yunlong Fan Xuhai Zhang Jing Chen Chaofan Jin Sisi Chen Liang Wang Quan Zhang Yue Chen |
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| Institution: | 1. State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Nankai University 38 Tongyan Road, Tianjin 300353 (P. R. China);2. State Key Laboratory of Medicinal Chemical Biology, College of Chemistry, Frontiers Science Center for New Organic Matter, Nankai University, 94 Weijin Road, Tianjin, 300071 P. R. China |
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| Abstract: | The total synthesis of the proposed structure of anti-glioblastoma natural product neaumycin B was achieved in 22 steps (longest linear sequence). The synthesis features HCl-mediated 6,6]-spiroketalization, a combination of Krische iridium-catalyzed crotylation, Marshall palladium-catalyzed propargylation, Fürstner nickel-catalyzed regio- and enantioselective vicinal monoprotected diol formation, Brown crotylation and asymmetric halide-aldehyde cycloaddition, so as to establish the challenging contiguous stereocenters. |
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| Keywords: | Antitumor Agents C−C Coupling Macrolide Natural Products Spiroketalization Total Synthesis |
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