Total syntheses of (±)-musellarins A-C

被引:26
|
作者
Li, Zhilong [1 ]
Leung, Tsz-Fai [1 ]
Tong, Rongbiao [1 ]
机构
[1] Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Hong Kong, Peoples R China
关键词
DE-NOVO SYNTHESIS; CATALYZED GLYCOSYLATION REACTION; FRIEDEL-CRAFTS CYCLIZATION; DIAZONIUM SALTS; NORHALICHONDRIN-B; HECK ARYLATION; METHYL-ESTER; PALLADIUM; REDUCTION; DERIVATIVES;
D O I
10.1039/c4cc05248j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first, diastereoselective total syntheses of musellarins A-C were achieved concisely with 7.8-9.8% yields in 15-16 steps. The key synthetic features include (i) an Achmatowicz rearrangement, Kishi reduction, and Friedel-Crafts cyclization to construct the tricyclic framework and (ii) Heck coupling of aryldiazonium salts to introduce the aryl group into the dihydropyran in a 2,6-trans fashion in the final stage of synthesis.
引用
收藏
页码:10990 / 10993
页数:4
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