Total synthesis of flustramine C via dimethylallyl rearrangement

被引：56

作者：

Lindel, Thomas ^{[1
]}

Braeuchle, Laura ^{[1
]}

Golz, Gregor ^{[1
]}

Boehrer, Petra ^{[1
]}

机构：

[1] Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 02期

关键词：

D O I：

10.1021/ol0627348

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHIC] The marine natural product flustramine C from the bryozoan Flustra foliacea was synthesized in five steps and 38% yield starting from N-b-methyltryptamine. The key step is the biomimetic oxidation of the natural product deformylflustrabromine causing selective 1,2-rearrangement of the inverse prenyl group. By H-1,N-15 HMBC experiments, it is unambiguously shown that the reaction with t-BuOCl commences with chlorination of the side chain nitrogen. Deformylflustrabromine itself was synthesized via Danishefsky inverse prenylation.

引用

页码：283 / 286

页数：4

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