Total synthesis of (-)-deglycocadambine

被引：0

作者：

Wang, Fang-Xin ^{[1
]}

Chen, Ying-Tao ^{[1
]}

Liu, Hui ^{[1
]}

Wang, Heng-Shan ^{[1
]}

Liang, Hong ^{[1
]}

Chen, Zhen-Feng ^{[1
]}

Chi, Yonggui Robin ^{[2
,3
]}

机构：

[1] Guangxi Normal Univ, Collaborat Innovat Ctr Guangxi Ethn Med, Sch Chem & Pharmaceut Sci,Minist Educ China, State Key Lab Chem & Mol Engn Med Resources, Guilin 541004, Peoples R China

[2] Nanyang Technol Univ, Sch Chem Chem Engn & Biotechnol, Singapore 637371, Singapore

[3] Guizhou Univ, Natl Key Lab Green Pesticide, Key Lab Green Pesticide & Agr Bioengn, Minist Educ, Huaxi Dist, Guiyang 550025, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2024年 / 11卷 / 17期

基金：

中国国家自然科学基金; 新加坡国家研究基金会;

关键词：

INDOLE ALKALOIDS;

D O I：

10.1039/d4qo01122h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of the monoterpene indole alkaloid (-)-deglycocadambine is achieved in 12 steps with (+)-genipin as the chiral starting material. The reported synthetic approach is characterized by an orchestrated cascade annulation between tryptamine and the highly functionalized dialdehyde precursor, rapidly introducing the unique 6/5/6/7/6-fused pentacyclic skeleton and the ketone functional group at C19 in a convergent manner. The successful implementation of transannular oxidative cyclization at C3 for bridged oxazolidine formation in the late-stage synthetic campaign ensured the final total synthesis of this molecule. The first total synthesis of (-)-deglycocadambine is achieved from (+)-genipin, wherein the well-designed cascade annulation and the late-stage transannular oxidative cyclization clearly unveil the bond-forming logic in this synthetic route.

引用

页码：4869 / 4873

页数：5

共 18 条

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