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Boc保护的双环脯氨酸的合成。

Synthesis of Boc-protected bicycloproline.

作者信息

Ranatunga Sujeewa, Del Valle Juan R

机构信息

Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces, NM 88003.

出版信息

Tetrahedron Lett. 2009 May 27;50(21):2464-2466. doi: 10.1016/j.tetlet.2009.03.092.

DOI:10.1016/j.tetlet.2009.03.092
PMID:20090865
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2808134/
Abstract

The synthesis of a highly constrained quaternary carbocyclic α-amino acid, (+)-N-Boc-bicycloproline, has been achieved starting from sodium cyclopentadienylide. Key steps include a rhodium-catalyzed nitrenoid C-H insertion to install the tert-alkylamine and a ring-closing metathesis reaction to form the pyrrolidine ring.

摘要

从环戊二烯基钠出发,已实现了一种高度受限的季碳环α-氨基酸(+)-N-Boc-双环脯氨酸的合成。关键步骤包括铑催化的氮宾C-H插入反应以引入叔烷基胺,以及闭环复分解反应以形成吡咯烷环。

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本文引用的文献

1
Stereoselective Synthesis of Quaternary Proline Analogues.季铵型脯氨酸类似物的立体选择性合成
European J Org Chem. 2008;20:3427-3448. doi: 10.1002/ejoc.200800225.
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Intrinsic conformational preferences of C(alpha,alpha)-dibenzylglycine.α,α-二苄基甘氨酸的固有构象偏好
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1-amino-2-phenylcyclopentane-1-carboxylic acid: a conformationally restricted phenylalanine analogue.1-氨基-2-苯基环戊烷-1-羧酸:一种构象受限的苯丙氨酸类似物。
J Org Chem. 2008 Jan 18;73(2):644-51. doi: 10.1021/jo702107s. Epub 2007 Dec 15.
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Silver-catalyzed intermolecular amination of C--H groups.银催化的C-H基团分子间胺化反应
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Design and synthesis of chiral alpha,alpha-disubstituted amino acids and conformational study of their oligopeptides.手性α,α-二取代氨基酸的设计与合成及其寡肽的构象研究
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Effect of substitution on the intramolecular 1,3-dipolar cycloaddition of alkene tethered münchnones.取代基对烯烃连接的慕尼黑酮分子内1,3-偶极环加成反应的影响。
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Recent approaches towards the asymmetric synthesis of alpha,alpha-disubstituted alpha-amino acids.α,α-二取代α-氨基酸不对称合成的最新方法。
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Culicinin D, an antitumor peptaibol produced by the fungus Culicinomyces clavisporus, strain LL-12I252.库利西宁D,一种由真菌克拉维孢库利西诺菌LL-12I252菌株产生的抗肿瘤肽菌素。
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