Consecutive Diels-Alder approach toward a Tet repressor directed combinatorial library

被引：10

作者：

Kormann, Christian

Heinemann, Frank W.

Gmeiner, Peter

机构：

[1] Univ Erlangen Nurnberg, Dept Med Chem, D-91052 Erlangen, Germany

[2] Univ Erlangen Nurnberg, Dept Inorgan Chem, D-91052 Erlangen, Germany

来源：

TETRAHEDRON | 2006年 / 62卷 / 29期

关键词：

solution phase parallel synthesis; Diels-Alder; tetracycline; TetR;

D O I：

10.1016/j.tet.2006.04.092

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A combinatorial library of 180 tetracycline analogs was generated by solution phase parallel synthesis applying a consecutive Diels-Alder strategy. Chemical methodology suitable for three-dimensional solution phase parallel synthesis was developed that enabled us to generate a collection of potential TetR inducers. The synthesis was built on cross-conjugated trienes as central building blocks facilitating two consecutive cycloaddition processes with different dienophiles. Upon sequential exposure to naphthoquinone and maleimide derivatives, the generation of a carbocyclic skeleton of type 2 incorporating the diversity elements R-1-R-5 was envisaged. (c) 2006 Elsevier Ltd. All rights reserved.

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收藏

页码：6899 / 6908

页数：10

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