Total Synthesis of Four Classes of Daphniphyllum Alkaloids

被引：18

作者：

Zhang, Wenhao ^{[1
]}

Lu, Ming ^{[1
]}

Ren, Lu ^{[1
]}

Zhang, Xiang ^{[1
]}

Liu, Shaonan ^{[1
]}

Ba, Mengyu ^{[1
,2
,3
]}

Yang, Peng ^{[2
,3
]}

Li, Ang ^{[1
,2
,3
]}

机构：

[1] Chinese Acad Sci, Univ Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Chem Biol, Shanghai 200032, Peoples R China

[2] Zhengzhou Univ, Henan Inst Adv Technol, Zhengzhou 450001, Peoples R China

[3] Zhengzhou Univ, Coll Chem, Zhengzhou 450001, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2023年 / 145卷 / 49期

基金：

中国国家自然科学基金;

关键词：

BIOMIMETIC TOTAL-SYNTHESIS; PENTACYCLIC ALKALOIDS; DAPHNICYCLIDIN; CHEMISTRY; OXIDATION; HYDROGENATION; CYCLOPROPANE; SYSTEM; RINGS;

D O I：

10.1021/jacs.3c06088

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The macrodaphniphyllamine-type, calyciphylline A-type, daphnilongeranin A-type, and daphnicyclidin D-type alkaloids are four structurally related classes of Daphniphyllum alkaloids. On the basis of a systematic analysis of the biogenetic network of these classes, we developed synthetic strategies centered on the C4-N and C1-C8 bonds of calyciphylline A, which took full advantage of the suitable substrates, reactions, and pathways that are altered from their counterparts in the postulated biogenetic network. Through this generalized biomimetic approach, we achieved the first synthesis of 14 Daphniphyllum alkaloids from the four subfamilies.

引用

页码：26569 / 26579

页数：11

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