A Concise Total Synthesis of Breitfussin A and B

被引：29

作者：

Pandey, Sunil Kumar ^{[1
,2
]}

Guttormsen, Yngve ^{[3
]}

Haug, Bengt Erik ^{[1
,2
]}

Hedberg, Christian ^{[4
,5
]}

Bayer, Annette ^{[3
]}

机构：

[1] Univ Bergen, Dept Chem, NO-5007 Bergen, Norway

[2] Univ Bergen, Ctr Pharm, NO-5007 Bergen, Norway

[3] UiT Arctic Univ Norway, Dept Chem, NO-9037 Tromso, Norway

[4] Max Planck Inst Mol Physiol, Dept Biol Chem, DE-44227 Dortmund, Germany

[5] Umea Univ, Dept Chem, S-90187 Umea, Sweden

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 01期

关键词：

CYTOTOXIC METABOLITES; DIAZONAMIDE; MICROSCOPY; INHIBITORS; OXAZOLES; REVISION;

D O I：

10.1021/ol503348n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of breitfussin A and B is described. The approach features two palladium-catalyzed cross-couplings installing the indole and pyrrole onto the oxazole core and selective lithiation/iodination of a common indole-oxazole fragment providing 2,4-diiodinated or 2-iodinated oxazoles as potential precursors for breitfussin A and B, respectively. An unexpected acid promoted deiodination was utilized in the synthesis of breitfussin B. Comparison of the synthetic material with previously reported spectral data of isolated breitfussin A and B verified the structure of the breitfussin framework.

引用

页码：122 / 125

页数：4

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