Synthesis of Atisine, Ajaconine, Denudatine, and Hetidine Diterpenoid Alkaloids by a Bioinspired Approach

被引：50

作者：

Li, Xiao-Huan ^{[1
,2
]}

Zhu, Min ^{[1
,2
]}

Wang, Zhi-Xiu ^{[1
,2
]}

Liu, Xiao-Yu ^{[1
,2
]}

Song, Hao ^{[1
,2
]}

Zhang, Dan ^{[1
,2
]}

Wang, Feng-Peng ^{[1
,2
]}

Qin, Yong ^{[1
,2
]}

机构：

[1] Sichuan Univ, Key Lab Drug Targeting & Drug Delivery Syst, West China Sch Pharm, Minist Educ, Chengdu 610041, Peoples R China

[2] Sichuan Univ, State Key Lab Biotherapy, Chengdu 610041, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 50期

基金：

中国国家自然科学基金;

关键词：

alkaloids; biomimetic synthesis; cyclization; terpenoids; total synthesis; STEREOSPECIFIC TOTAL-SYNTHESIS; C-20-DITERPENOID ALKALOIDS; CONSTRUCTION; STRATEGIES; 1,3-DITHIANES; (+/-)-ATISINE; TALATISAMINE; CARBANIONS; GENERATION; SPIRAMINES;

D O I：

10.1002/anie.201609882

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A unified approach to four different (atisine, ajaconine, denudatine, and hetidine) diterpenoid alkaloid skeletons was developed and applied to the total synthesis of the natural products dihydroajaconine (2, atisine type) and gymnandine (4, denudatine type). The synthesis features a biogenetically inspired strategy that relies on C-H oxidation, aza-pinacol coupling, and aza-Prins cyclization as key steps.

引用

页码：15667 / 15671

页数：5

共 81 条

[51] Enantioselective Photoredox Catalysis Enabled by Proton-Coupled Electron Transfer: Development of an Asymmetric Aza-Pinacol Cyclization [J].