Synthesis of (±)-pterosin A via Suzuki-Miyaura cross-coupling reaction

被引：12

作者：

Hsu, Shao-Chien ^{[1
]}

Narsingam, Mogili ^{[1
]}

Lin, Yi-Fang ^{[1
]}

Hsu, Feng-Lin ^{[2
]}

Uang, Biing-Jiun ^{[1
]}

机构：

[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan

[2] Taipei Med Univ, Sch Pharm, Grad Inst Pharmacognosy, Taipei 110, Taiwan

来源：

TETRAHEDRON | 2013年 / 69卷 / 12期

关键词：

Suzuki-Miyaura reaction; Vinylation; Potassium vinyltrifluoroborate; Pterosin A; AQUILINUM-VAR-LATIUSCULUM; ARYL BROMIDES; BRACKEN FERN; POTASSIUM VINYLTRIFLUOROBORATE; PTEROSIN FAMILY; SESQUITERPENES; CONSTITUENTS; DERIVATIVES; GENERATION; VINYLATION;

D O I：

10.1016/j.tet.2013.01.055

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical synthesis of (+/-)-pterosin A from commercially available 2-bromo-1,3-dimethyl-benzene 5 has been accomplished in 10% overall yield. The synthesis used Suzuki-Miyaura coupling reaction of C6-bromoindanone derivative 3 with potassium vinyltrifluoroborate 9, which provided the corresponding vinylindanone 2 in >85% yield. The vinylindanone 2 could be further elaborated to pterosin A by reduction with LAH, selective protection of primary alcohol with TESCI, hydroboration-oxidation of vinyl group, protection of primary alcohol with TIPSCI, oxidation of the secondary alcohol, and desilylation with TBAF. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：2572 / 2576

页数：5

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