Total Synthesis of Starfish Cyclic Steroid Glycosides. Part 2, Model Synthesis via Intramolecular Etherification

被引：7

作者：

Chen, Youxi ^{[1
]}

Xiao, Guozhi ^{[1
,2
]}

Zhu, Dapeng ^{[1
]}

Yu, Biao ^{[1
]}

机构：

[1] Univ Chinese Acad Sci, Chinese Acad Sci, Shanghai Inst Organ Chem, Ctr Excellence Mol Synth,State Key Lab Bioorgan &, Shanghai 200032, Peoples R China

[2] Univ Chinese Acad Sci, Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochemistry & Plant Resources Wes, Kunming 650201, Yunnan, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2023年 / 41卷 / 08期

基金：

中国国家自然科学基金;

关键词：

Cyclic starfish glycosides; Au(I) catalysis; Epoxide; Glycosylation; Cyclization; ALKYNYLBENZOATES;

D O I：

10.1002/cjoc.202200786

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Sepositoside A (1) is a prototypical cyclic steroid glycoside bearing a hybrid 16-membered ring composed of the steroid skeleton and a 1,2-trans-linked trisaccharide. Herein, we report an expedient access toward two simplified analogues, in which the strained 16-membered ring is constructed via Au(I)-catalyzed intramolecular addition of alcohol to epoxide. A similar macroetherification in relevant steroid trisaccharides has been intensively examined, however, failed to furnish the macrocyclic skeleton of Sepositoside A.

引用

页码：897 / 902

页数：6

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