Total Synthesis of Viridin and Viridiol

被引：62

作者：

Ji, Yang ^{[1
]}

Xin, Zhengyuan ^{[1
]}

He, Haibing ^{[2
]}

Gao, Shuanhu ^{[1
,2
]}

机构：

[1] East China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Sch Chem & Mol Engn, 3663N Zhongshan Rd, Shanghai 200062, Peoples R China

[2] East China Normal Univ, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, 3663N Zhongshan Rd, Shanghai 200062, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2019年 / 141卷 / 41期

基金：

中国国家自然科学基金;

关键词：

ALKENE CYCLOADDITION; SECONDARY ALCOHOLS; INHIBITOR; OXIDATION; OLEFINS; CONVERSION; FE;

D O I：

10.1021/jacs.9b08577

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The asymmetric total synthesis of (-)-viridin and (-)-viridiol, antifungal metabolites, was achieved in 17 and 18 steps from a commercially available starting material. An intramolecular [3+2] cycloaddition was applied to an easily available L-ribose derivative in order to construct the highly substituted D ring containing the key chiral cis-triol fragment. Co-catalyzed metal-hydride H atom transfer (MHAT) radical cyclization was utilized to form the C-ring and the all-carbon quaternary center at C-10. This convergent strategy provides a scalable approach to prepare viridin and viridiol for biological studies.

引用

页码：16208 / 16212

页数：5

共 59 条

[1] DEMETHOXYVIRIDIN AND DEMETHOXYVIRIDIOL - NEW FUNGAL METABOLITES [J].