Consecutive isocyanide-based multicomponent reactions: synthesis of cyclic pentadepsipeptoids

被引：27

作者：

Barreto, Angelica de Fatima S. ^{[1
]}

Vercillo, Otilie E. ^{[2
]}

Wessjohann, Ludger A. ^{[3
]}

Andrade, Carlos Kleber Z. ^{[1
]}

机构：

[1] Univ Brasilia, Inst Quim, Lab Quim Metodol & Organ Sintet, BR-70910970 Brasilia, DF, Brazil

[2] Fac UnB Planaltina, BR-73300000 Brasilia, DF, Brazil

[3] Leibniz Inst Plant Biochem, Dept Bioorgan Chem, D-06120 Halle, Saale, Germany

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 10卷

关键词：

depsipeptoids; multicomponent reactions; Passerini reaction; sansalvamide A; Ugi reaction; SANSALVAMIDE-A DERIVATIVES; ANTITUMOR AGENTS; UGI REACTIONS; SOLID-PHASE; PEPTOIDS; PEPTIDE; POTENT; DEPSIPEPTIDES; ANALOGS; CYTOTOXICITY;

D O I：

10.3762/bjoc.10.101

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of six cyclic depsipeptoids inspired by the natural depsipeptide sansalvamide A is described. An efficient and fast synthetic strategy was developed using a combination of consecutive isocyanide-based multicomponent reactions (Ugi and Passerini reactions). This methodology can be used to access a variety of cyclic oligodepsipeptoids.

引用

页码：1017 / 1022

页数：6

共 46 条

[1] Structural analysis of peptide helices containing centrally positioned lactic acid residues [J].

Aravinda, S ;

Shamala, N ;

Das, C ;

Balaram, P .

BIOPOLYMERS, 2002, 64 (05) :255-267

[2] Macrocycles That Inhibit the Binding between Heat Shock Protein 90 and TPR-Containing Proteins [J].

Ardi, Veronica C. ;

Alexander, Leslie D. ;

Johnson, Victoria A. ;

McAlpine, Shelli R. .

ACS CHEMICAL BIOLOGY, 2011, 6 (12) :1357-1366

[3]

Barreto A. F. S., 2013, THESIS U BRASILIA BR

[4]

Barreto A. F. S., 2011, BLUCHER CHEM P, V1, P298

[5] Fast and efficient microwave-assisted synthesis of functionalized peptoids via Ugi reactions [J].

Barreto, Angelica de Fatima S. ;

Vercillo, Otilie E. ;

Birkett, Mike A. ;

Caulfield, John C. ;

Wessjohann, Ludger A. ;

Andrade, Carlos Kleber Z. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (14) :5024-5027

[6]

Barreto ADS, 2011, J BRAZIL CHEM SOC, V22, P462, DOI 10.1590/S0103-50532011000300008

[7] Sansalvamide: A new cytotoxic cyclic depsipeptide produced by a marine fungus of the genus Fusarium [J].

Belofsky, GN ;

Jensen, PR ;

Fenical, W .

TETRAHEDRON LETTERS, 1999, 40 (15) :2913-2916

[8] α-amino acids as acid components in the Passerini reaction:: influence of N-protection on the yield and stereoselectivity [J].

Berlozecki, Stanislaw ;

Szymanski, Wiktor ;

Ostaszewski, Ryszard .

TETRAHEDRON, 2008, 64 (41) :9780-9783

[9] Synthesis and cytotoxicity of novel sansalvamide A derivatives [J].

Carroll, CL ;

Johnston, JVC ;

Kekec, A ;

Brown, JD ;

Parry, E ;

Cajica, J ;

Medina, I ;

Cook, KM ;

Corral, R ;

Pan, PS ;

McAlpine, SR .

ORGANIC LETTERS, 2005, 7 (16) :3481-3484

[10] Synthesis and cytotoxicity of a new class of potent decapeptide macrocycles [J].

Davis, Melinda R. ;

Styers, Thomas J. ;

Rodriguez, Rodrigo A. ;

Pan, Po-Shen ;

Vasko, Robert C. ;

McAlpine, Shelli R. .

ORGANIC LETTERS, 2008, 10 (02) :177-180

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