A convenient strategy for synthesizing the Agelas alkaloids clathrodin, oroidin, and hymenidin and their (un)saturated linker analogs

被引：9

作者：

Zula, Ales ^{[1
]}

Kikelj, Danijel ^{[1
]}

Ilas, Janez ^{[1
]}

机构：

[1] Univ Ljubljana, Fac Pharm, Ljubljana 1000, Slovenia

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 29期

关键词：

Clathrodin; Oroidin; Hymenidin; Agelas species; Synthetic analogs; 2-AMINOIMIDAZOLE MARINE METABOLITES; PYRROLE-IMIDAZOLE ALKALOIDS; SPONGE; DERIVATIVES; TOXINS;

D O I：

10.1016/j.tetlet.2014.05.087

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient strategy for the scalable synthesis of the 2-aminoimidazole alkaloids, clathrodin, oroidin, and hymenidin derived from marine Agelas species and their analogs possessing a saturated or unsaturated linker moiety is described. The key intermediates, 4-(3-aminopropyl)-1H-imidazol-2-amine and (E)-4-(3-aminoprop-1-en-1-yl)-1H-imidazol-2-amine were obtained through two different synthetic pathways starting from L-omithine and benzyl 1,2-dihydropyridine-1-carboxylate respectively, using (i) an innovative combination of Weinreb amide strategy with di-Boc protection, and (ii) a modified pyridine-1(2H)-carboxylate based strategy. Convenient access to these 2-aminoimidazole amines is crucial for the synthesis of libraries of clathrodin, oroidin, and hymenidin analogs. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：3999 / 4001

页数：3

共 29 条

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