A Ten-Step Total Synthesis of SperadineC

被引：25
|
作者：
Liu, Haichao [1 ]
Chen, Lijun [1 ]
Yuan, Kuo [1 ]
Jia, Yanxing [1 ]
机构：
[1] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Xue Yuan Rd 38, Beijing 100191, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 19期
基金：
中国国家自然科学基金;
关键词：
cascade cyclization; indole alkaloids; natural products; oxidative cyclization; total synthesis; 3,4-FUSED TRICYCLIC INDOLES; CYCLOPIAZONIC ACID; ENANTIOSELECTIVE SYNTHESIS; ASPERGILLUS-FLAVUS; OXINDOLE; ALKALOIDS; (+/-)-SEROTOBENINE; TRANSFORMATION; OXIDATION;
D O I：
10.1002/anie.201902004
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The first total synthesis of speradineC has been achieved in only ten steps from a commercially available 4-bromoindole. Salient features of the work are the formation of four rings through three cyclizations, namely a bioinspired [3+2] annulation to form the C/D rings, an NCS-mediated oxidation to construct the Ering, and a Ru-catalyzed ketohydroxylation to assemble the Fring. This work highlights how strategic ring constructions can streamline the synthesis of polycyclic compounds.
引用
收藏
页码：6362 / 6365
页数：4
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