Bioinspired Collective Total Synthesis of (±)-Rhynchines A-E

被引：4

作者：

Guo, Xiao-Feng ^{[1
,2
]}

Shao, Hui ^{[1
,2
]}

Ma, Zhi-Hua ^{[1
,2
]}

Sun, Jian ^{[1
,2
]}

Zhou, Qin ^{[1
,2
]}

Zhao, Yu-Ming ^{[1
,2
]}

机构：

[1] Shaanxi Normal Univ, Key Lab Appl Surface & Colloid Chem MOE, Xian 710119, Peoples R China

[2] Shaanxi Normal Univ, Sch Chem & Chem Engn, Xian, Peoples R China

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 15期

基金：

中国国家自然科学基金;

关键词：

INDOLE ALKALOIDS; CARBON NUCLEOPHILES;

D O I：

10.1021/acs.orglett.4c00727

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we present the first racemic total synthesis of the structurally complex monoterpene indole alkaloids rhynchines A-E, starting from commercially available methyl nicotinate and 3-(2-bromoethyl)-1H-indole. The success of our synthesis is attributed to the utilization of a bioinspired synthetic strategy, which facilitated the rapid construction of the pentacyclic core skeleton of the target molecules through biomimetic skeletal rearrangement and late-stage C-H oxidative cyclization. Additionally, silica-gel-promoted tautomerization played a crucial role as a strategic element in the chemical synthesis of rhynchines A and B.

引用

页码：3135 / 3139

页数：5

共 16 条

[11] Halogen bond-induced electrophilic aromatic halogenations [J].