Enantioselective Palladium-Catalyzed Decarboxylative Allylation of Carbazolones: Total Synthesis of (-)-Aspidospermidine and (+)-Kopsihainanine A

被引：105

作者：

Li, Zeqian ^{[1
]}

Zhang, Shaoxiong ^{[1
]}

Wu, Shoutao ^{[1
]}

Shen, Xiaolei ^{[1
]}

Zou, Liwei ^{[1
]}

Wang, Fengqun ^{[1
]}

Li, Xiang ^{[1
]}

Peng, Fangzhi ^{[1
]}

Zhang, Hongbin ^{[1
]}

Shao, Zhihui ^{[1
]}

机构：

[1] Yunnan Univ, Sch Chem Sci & Technol, Minist Educ, Key Lab Med Chem Nat Resource, Kunming 650091, Yunnan, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 15期

关键词：

aspidospermidine; asymmetric catalysis; total synthesis; kopsihainanineA; natural products; ASYMMETRIC ALLYLIC ALKYLATION; INTRAMOLECULAR SCHMIDT REACTION; QUATERNARY CARBON CENTERS; CROSS-COUPLING REACTION; FORMAL TOTAL SYNTHESIS; ASPIDOSPERMA ALKALOIDS; INDOLE ALKALOIDS; DL-ASPIDOSPERMIDINE; NATURAL-PRODUCTS; CARROLL REARRANGEMENT;

D O I：

10.1002/anie.201209878

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Functionalized chiral carbazolones with α-quaternary carbon centers are formed through the ligand-controlled Pd-catalyzed enantioselective decarboxylative allylic alkylation of carbazolones (see scheme). This catalytic asymmetric reaction was employed as the key step in the total synthesis of aspidospermidine and (+)-kopsihainanineA. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：4117 / 4121

页数：5

共 114 条

[11] Asymmetric allylic alkylation of ketone enolates: An asymmetric claisen surrogate [J].