Synthesis of the pyrrole-imidazole alkaloid sventrin from the marine sponge Agelas sventres

被引：12

作者：

Breckle, G ^{[1
]}

Polborn, K ^{[1
]}

Lindel, T ^{[1
]}

机构：

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

来源：

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES | 2003年 / 58卷 / 05期

关键词：

alkynes; Red-Al; marine natural products;

D O I：

10.1515/znb-2003-0516

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The marine pyrrole-imidazole alkaloid sventrin (1) and the hitherto unknown dehydrooroidin (3) have been synthesized stereoselectively via alkyne intermediates. The pathways start from a 2-azido-4-alkynylimidazole which can be chemo- and stereoselectively reduced to the corresponding amino alkene using NaAlH2(OCH2CH2OMe)(2) (Red-Al) or, alternatively, to the amino alkyne. Selective removal of simultaneously present Boc or trityl protecting groups was possible employing either p-TsOH or acetic resp. formic acid.

引用

页码：451 / 456

页数：6

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