Total Synthesis of the Proposed Structure of Neaumycin B
Sen Zhang
State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Nankai University 38 Tongyan Road, Tianjin 300353 (P. R. China)
Search for more papers by this authorSongming Zhang
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
Search for more papers by this authorYunlong Fan
State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Nankai University 38 Tongyan Road, Tianjin 300353 (P. R. China)
Search for more papers by this authorXuhai Zhang
State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Nankai University 38 Tongyan Road, Tianjin 300353 (P. R. China)
Search for more papers by this authorJing Chen
State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Nankai University 38 Tongyan Road, Tianjin 300353 (P. R. China)
Search for more papers by this authorChaofan Jin
State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Nankai University 38 Tongyan Road, Tianjin 300353 (P. R. China)
Search for more papers by this authorSisi Chen
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
Search for more papers by this authorCorresponding Author
Liang Wang
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
Search for more papers by this authorCorresponding Author
Quan Zhang
State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Nankai University 38 Tongyan Road, Tianjin 300353 (P. R. China)
Search for more papers by this authorCorresponding Author
Yue Chen
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
Search for more papers by this authorSen Zhang
State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Nankai University 38 Tongyan Road, Tianjin 300353 (P. R. China)
Search for more papers by this authorSongming Zhang
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
Search for more papers by this authorYunlong Fan
State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Nankai University 38 Tongyan Road, Tianjin 300353 (P. R. China)
Search for more papers by this authorXuhai Zhang
State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Nankai University 38 Tongyan Road, Tianjin 300353 (P. R. China)
Search for more papers by this authorJing Chen
State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Nankai University 38 Tongyan Road, Tianjin 300353 (P. R. China)
Search for more papers by this authorChaofan Jin
State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Nankai University 38 Tongyan Road, Tianjin 300353 (P. R. China)
Search for more papers by this authorSisi Chen
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
Search for more papers by this authorCorresponding Author
Liang Wang
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
Search for more papers by this authorCorresponding Author
Quan Zhang
State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Nankai University 38 Tongyan Road, Tianjin 300353 (P. R. China)
Search for more papers by this authorCorresponding Author
Yue Chen
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
Search for more papers by this authorAbstract
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.
Conflict of interest
The authors declare no conflict of interest.
Open Research
Data Availability Statement
The data that support the findings of this study are available in the supplementary material of this article.
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