Transannular rearrangement of activated 2,5-diketopiperazines: a key route to original scaffolds

被引：29

作者：

Farran, Daniel ^{[1
]}

Parrot, Isabelle ^{[1
]}

Toupet, Loic ^{[2
]}

Martinez, Jean ^{[1
]}

Dewynter, Georges ^{[1
]}

机构：

[1] Univ Montpellier 2, Univ Montpellier 1, Inst Biomol Max Mousseron, UMR CNRS 5247, F-34095 Montpellier 5, France

[2] Univ Rennes 1, Grp Mat Condensee & Mat, UMR6626, F-35042 Rennes, France

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2008年 / 6卷 / 21期

关键词：

D O I：

10.1039/b810352f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and original stereocontrolled transannular rearrangement starting from activated 2,5-diketopiperazines has been developed, an opportunity for the medicinal chemistry field, which requests access to novel biological scaffolds. This powerful ring contraction, which can be related to a stereoselective aza-version of the Chan rearrangement, allows for example the one-step synthesis of various tetramic acids, access to 2-disubstituted statins, or the synthesis of relevant lactam-constrained dipeptide mimetics using a TRAL-RCM sequence.

引用

页码：3989 / 3996

页数：8

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