Synthesis of Natural Product-like Polyheterocycles via One-Pot Cascade Oximation, C-H Activation, and Alkyne Annulation

被引：40

作者：

Zheng, Liyao ^{[1
]}

Bin, Yunhui ^{[1
]}

Wang, Yunpeng ^{[1
]}

Hua, Ruimao ^{[1
]}

机构：

[1] Tsinghua Univ, Dept Chem, Minist Educ, Key Lab Organ Optoelect & Mol Engn, Beijing 100084, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 19期

基金：

中国国家自然科学基金;

关键词：

CATALYZED INTRAMOLECULAR ANNULATION; DIVERSITY-ORIENTED SYNTHESIS; HETERO-DIELS-ALDER; CASSIA-SIAMEA; BOND ACTIVATION; DRUG DISCOVERY; PRIVILEGED STRUCTURES; RHODIUM CATALYSIS; ANTITUMOR AGENTS; CHEMICAL SPACE;

D O I：

10.1021/acs.joc.6b01460

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient protocol for the direct transformation of chrornan-4-ones to tricyclic fused pyridines with the skeleton of cassiarins, a family of alkaloids with antimalarial activity, was developed. Also, a general strategy for modular construction of polyheterocydes with diverse natural product-like skeletons was developed by using ketone-alkyne bifunctional substrates. These reactions involved a one-pot cascade oximation of ketones, rhodium-catalyzed C-H activation, and intermolecular/intramolecular alkyne annulations under mild conditions with high atom, step, and redox economy.

引用

页码：8911 / 8919

页数：9