Skeletal diversity by sequential one-pot and stepwise routes using morpholine ester scaffolds

被引：25

作者：

Ciofi, Leonardo ^{[1
]}

Morvillo, Manfredi ^{[1
]}

Sladojevich, Filippo ^{[2
]}

Guarna, Antonio ^{[1
]}

Trabocchi, Andrea ^{[1
]}

机构：

[1] Univ Florence, Dept Chem Ugo Schiff, I-50019 Florence, Italy

[2] Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 48期

关键词：

Chemical diversity; Amino acids; Peptidomimetics; Combinatorial Chemistry; Heterocycles; SMALL MOLECULES; DERIVATIVES; DIKETOPIPERAZINE; 3-COMPONENT; ALKYLATION; INHIBITORS; ACCESS; AGENT;

D O I：

10.1016/j.tetlet.2010.09.103

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A skeletal diversity approach starting from morpholine acetals has been achieved by tuning a three-step process from stepwise to sequential one-pot to provide diverse scaffolds containing either a 2-oxopiperazine or a diketopiperazine skeleton. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：6282 / 6285

页数：4

共 42 条

[31] Sequential One-Pot Cyclizations: Concise Access to the ABCE Tetracyclic Framework of Strychnos Alkaloids [J].

Sirasani, Gopal ;

Andrade, Rodrigo B. .

ORGANIC LETTERS, 2009, 11 (10) :2085-2088

[32] Stereoselective cyclopropanation of serine- and threonine-derived oxazines to access new morpholine-based scaffolds [J].

Sladojevich, Filippo ;

Trabocchi, Andrea ;

Guarna, Antonio .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (18) :3328-3336

[33] Convenient route to enantiopure fmoc-protected morpholine-3-carboxylic acid [J].

Sladojevich, Filippo ;

Trabocchi, Andrea ;

Guarna, Antonio .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (11) :4254-4257

[34] Evaluation of stereochemically dense morpholine-based scaffolds as proline surrogates in β-turn peptides [J].

Sladojevich, Filippo ;

Guarna, Antonio ;

Trabocchi, Andrea .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (04) :916-924

[35] Anti-MRSA agent discovery using diversity-oriented synthesis [J].

Thomas, Gemma L. ;

Spandl, Richard J. ;

Glansdorp, Freija G. ;

Welch, Martin ;

Bender, Andreas ;

Cockfield, Joshua ;

Lindsay, Jodi A. ;

Bryant, Clare ;

Brown, Derek F. J. ;

Loiseleur, Olivier ;

Rudyk, Helene ;

Ladlow, Mark ;

Spring, David R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (15) :2808-2812

[36] Configurationally Driven Folding of Model Tetrapeptides Containing L- or D-Morpholine-3-carboxylic acids as β-Turn Nucleators [J].

Trabocchi, Andrea ;

Sladojevich, Filippo ;

Guarna, Antonio .

CHIRALITY, 2009, 21 (06) :584-594

[37] Regioselective one-pot protection of carbohydrates [J].

Wang, Cheng-Chung ;

Lee, Jinq-Chyi ;

Luo, Shun-Yuan ;

Kulkarni, Suvarn S. ;

Huang, Yu-Wen ;

Lee, Chia-Chen ;

Chang, Ken-Lien ;

Hung, Shang-Cheng .

NATURE, 2007, 446 (7138) :896-899

[38]

Wennemers H, 2001, CHEM-EUR J, V7, P3342, DOI 10.1002/1521-3765(20010803)7:15<3342::AID-CHEM3342>3.0.CO

[39]

2-7

[40] Fluorous, Parallel Synthesis of a Piperazinedione-Fused Tricyclic Compound Library [J].

Werner, Stefan ;

Nielsen, Simon D. ;

Wipf, Peter ;

Turner, David M. ;

Chambers, Peter G. ;

Geib, Steven J. ;

Curran, Dennis P. ;

Zhang, Wei .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2009, 11 (03) :452-459

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