Asymmetric Total Syntheses of Sarglamides A, C, and E

被引：0

作者：

Wang, Xinyu ^{[1
]}

Yang, Yunxia ^{[1
]}

Fang, Jing ^{[1
]}

Duan, Jinbo ^{[1
]}

Xie, Xingang ^{[1
]}

Li, Huilin ^{[1
]}

She, Xuegong ^{[1
]}

机构：

[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 90卷 / 01期

基金：

中国国家自然科学基金;

关键词：

DERIVATIVES;

D O I：

10.1021/acs.joc.4c02666

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric total syntheses of sarglamides A, C, and E in concise and protecting group free fashion is disclosed. Key steps involve an endo-selective Diels-Alder reaction to construct the bicyclo[2.2.2]nonane framework, a nucleophilic addition and an intramolecular aza-Michael addition to install the pyrrolidine ring, and a final cinnamoylation reaction. Sarglamide C is biomimetically transformed into E through a Br & oslash;nsted acid mediated oxy-cyclization. Sarglamide D is also accessible from C based on Yue's research. This work provides an efficient asymmetric approach to the syntheses of sarglamides and also provides insights into understand the plausible biogenetic pathway of these monoterpenoid-indolidinoid hybrid structures.

引用

页码：709 / 715

页数：7

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