Synthesis of the trans-fusarinine scaffold

被引：7

作者：

Bertrand, Samuel ^{[1
]}

Duval, Olivier ^{[1
]}

Helesbeux, Jean-Jacques ^{[1
]}

Larcher, Gerald ^{[2
]}

Richomme, Pascal ^{[1
]}

机构：

[1] Univ Angers, UFR Sci Pharmaceut & Ingn Sante, Lab Subst Origine Nat & Analogues Struct, UPRES EA 921,IFR 149,QUASAV, F-49045 Angers, France

[2] Univ Angers, UFR Sci Pharmaceut & Ingn Sante, Grp Etud Interact Hote Parasite, UPRES EA 3142,IFR 132, F-49045 Angers, France

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 16期

关键词：

Siderophore; Fusarinine; Multi-step synthesis; IRON CHELATORS; SIDEROPHORES; DESIGN;

D O I：

10.1016/j.tetlet.2010.02.058

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The trans-fusarinine backbone is a common feature encountered in many fungal siderophores. This monomer is notably the structural base of N-alpha-methyl coprogen B and dimerumic acid. Both siderophores are known to be secreted by Scedosporium apiospermum, an emerging pathogenic fungus studied for its high involvement in invasive infections of immunocompromised patients. The strategy developed here for the synthesis of the trans-fusarinine scaffold relies on the preparation of both N-hydroxyornithine and 3-anhydroxymevalonic acid subunits starting from L-ornithine and 3-butyn-1-ol, respectively. The coupling of these two building blocks led to the expected protected backbone. (c) 2010 Elsevier Ltd. All rights reserved.

引用

页码：2119 / 2122

页数：4

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