Total Synthesis of the Proposed Structure of Neaumycin B

被引：6

作者：

Zhang, Sen ^{[1
]}

Zhang, Songming ^{[2
]}

Fan, Yunlong ^{[1
]}

Zhang, Xuhai ^{[1
]}

Chen, Jing ^{[1
]}

Jin, Chaofan ^{[1
]}

Chen, Sisi ^{[2
]}

Wang, Liang ^{[2
]}

Zhang, Quan ^{[1
]}

Chen, Yue ^{[2
]}

机构：

[1] Nankai Univ, State Key Lab Med Chem Biol, Coll Pharm, 38 Tongyan Rd, Tianjin 300353, Peoples R China

[2] Nankai Univ, State Key Lab Med Chem Biol, Coll Chem, Frontiers Sci Ctr New Organ Matter, 94 Weijin Rd, Tianjin 300071, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2023年 / 62卷 / 51期

基金：

中国国家自然科学基金;

关键词：

Antitumor Agents; C-C Coupling; Macrolide Natural Products; Spiroketalization; Total Synthesis; ETHER TRANSFER; HYDROBORATION; CONVERSION; CONGENERS; MACROLIDE; ALDEHYDES; ALCOHOLS; ALKENYL; HALIDES; KETONES;

D O I：

10.1002/anie.202313186

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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, Furstner nickel-catalyzed regio- and enantioselective vicinal monoprotected diol formation, Brown crotylation and asymmetric halide-aldehyde cycloaddition, so as to establish the challenging contiguous stereocenters.

引用

页数：10

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