Divergent Total Syntheses of (-)-Daphnilongeranin B and (-)-Daphenylline

被引：74

作者：

Chen, Xiaoming ^{[1
]}

Zhang, Hai-Jun ^{[1
]}

Yang, Xinkan ^{[2
]}

Lv, Houqiang ^{[2
]}

Shao, Xiaoru ^{[1
]}

Tao, Cheng ^{[2
]}

Wang, Huifei ^{[1
]}

Cheng, Bin ^{[2
]}

Li, Yun ^{[2
]}

Guo, Jingjing ^{[2
]}

Zhang, Jing ^{[1
]}

Zhai, Hongbin ^{[1
,2
,3
]}

机构：

[1] Peking Univ, Shenzhen Grad Sch, Key Lab Chem Genom, Shenzhen Engn Lab Nano Drug Slow Release, Shenzhen 518055, Peoples R China

[2] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, 222 Tianshui South Rd, Lanzhou 730000, Gansu, Peoples R China

[3] Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300071, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 04期

基金：

中国博士后科学基金;

关键词：

alkaloids; asymmetric total synthesis; 3+2] cycloaddition; natural products; rearrangement; BIOMIMETIC TOTAL-SYNTHESIS; CARBON TRICYCLIC CORE; A-TYPE ALKALOIDS; DAPHNIPHYLLUM ALKALOIDS; TETRACYCLIC CORE; RING-SYSTEM; EXPEDIENT CONSTRUCTION; ASYMMETRIC-SYNTHESIS; RAPID CONSTRUCTION; FORMAL SYNTHESIS;

D O I：

10.1002/anie.201709762

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(-)-Daphnilongeranin B and (-)-daphenylline are two hexacyclic Daphniphyllum alkaloids, each containing a complex cagelike backbone. Described herein are the first asymmetric total synthesis of (-)-daphnilongeranin B and a bioinspired synthesis of (-)-daphenylline with an unusual E ring embedded in a cagelike framework. The key features include an intermolecular [3+2] cycloaddition, a late-stage aldol cyclization to install the F ring of daphnilongeranin B, and a bioinspired cationic rearrangement leading to the tetrasubstituted benzene ring of daphenylline.

引用

页码：947 / 951

页数：5

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