Synthesis of Fmoc-protected amino ketones bearing tert-butyl based side-chain protecting groups

被引：13

作者：

Vázquez, J

Albericio, F

机构：

[1] Univ Barcelona, Barcelona Biomed Res Inst, E-08028 Barcelona, Spain

[2] Univ Barcelona, Dept Organ Chem, E-08028 Barcelona, Spain

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 42期

关键词：

amino ketones; ketone synthesis; combinatorial chemistry; high-throughput synthesis;

D O I：

10.1016/S0040-4039(02)01805-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of Fmoc-protected amino ketones have been prepared in good yields from amino acids by their transformation into thioesters of 2-mercaptopyridine and reaction of the resulting products with dialkylcuprates. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：7499 / 7502

页数：4

相关论文

共 20 条

[1] Active carbonate resins: Application to the solid-phase synthesis of alcohol, carbamate and cyclic peptides [J].

Alsina, J ;

Rabanal, F ;

Chiva, C ;

Giralt, E ;

Albericio, F .

TETRAHEDRON, 1998, 54 (34) :10125-10152

[2] Peptide synthesis via amino acid halides [J].

Carpino, LA ;

Beyermann, M ;

Wenschuh, H ;

Bienert, M .

ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (06) :268-274

[3] A simple preparation of ketones.: N-protected α-amino ketones from α-amino acids [J].

De Luca, L ;

Giacomelli, G ;

Porcheddu, A .

ORGANIC LETTERS, 2001, 3 (10) :1519-1521

[4] Synthesis of ketones and aldehydes via reactions of Weinreb-type amides on solid support [J].

Dinh, TQ ;

Armstrong, RW .

TETRAHEDRON LETTERS, 1996, 37 (08) :1161-1164

[5] Enantiomerically pure highly functionalized alpha-amino ketones from the reaction of chiral cyclic N-(9-phenylfluoren-9-yl) alpha-amido esters with organolithium reagents [J].

FernandezMegia, E ;

IglesiasPintos, JM ;

Sardina, FJ .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (14) :4770-4779

[6] Inhibition of human caspases by peptide-based and macromolecular inhibitors [J].

Garcia-Calvo, M ;

Peterson, EP ;

Leiting, B ;

Ruel, R ;

Nicholson, DW ;

Thornberry, NA .

JOURNAL OF BIOLOGICAL CHEMISTRY, 1998, 273 (49) :32608-32613

[7] Death of dopaminergic neurons in vitro and in nigral grafts:: Reevaluating the role of caspase activation [J].

Hurelbrink, CB ;

Armstrong, RJE ;

Luheshi, LM ;

Dunnett, SB ;

Rosser, AE ;

Barker, RA .

EXPERIMENTAL NEUROLOGY, 2001, 171 (01) :46-58

[8] A NOVEL, CONVENIENT, 3-DIMENSIONAL ORTHOGONAL STRATEGY FOR SOLID-PHASE SYNTHESIS OF CYCLIC-PEPTIDES [J].

KATES, SA ;

SOLE, NA ;

JOHNSON, CR ;

HUDSON, D ;

BARANY, G ;

ALBERICIO, F .

TETRAHEDRON LETTERS, 1993, 34 (10) :1549-1552

[9] Potent and selective nonpeptide inhibitors of caspases 3 and 7 [J].

Lee, D ;

Long, SA ;

Murray, JH ;

Adams, JL ;

Nuttall, ME ;

Nadeau, DP ;

Kikly, K ;

Winkler, JD ;

Sung, CM ;

Ryan, MD ;

Levy, MA ;

Keller, PM ;

DeWolf, WE .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (12) :2015-2026

[10]

MERCK FROSST CAN, 2000, Patent No. 0032620