New application of the Julia olefination for the synthesis of Tyr-Gly E-alkene and carba isostere pseudopeptides

被引：10

作者：

Charrier, C ^{[1
]}

Ettouati, L ^{[1
]}

Paris, J ^{[1
]}

机构：

[1] Univ Lyon 1, Inst Sci Pharmaceut & Biol, Chim Therapeut Lab, F-69373 Lyon 08, France

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 31期

关键词：

D O I：

10.1016/S0040-4039(99)01139-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new application of the Julia olefination to the synthesis of Tyr Psi[E-CH=CH]Gly and Tyr Psi[CH2CH2]Gly pseudopeptides is described via condensation of tertiobutyl bromoacetate on tyrosine-derived beta-ketosulfone and subsequent reductive desulfonation. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：5705 / 5707

页数：3

共 11 条

[1] The gamma-methyl-E-olefin as isosteric replacement of the peptide bond [J].

Devadder, S ;

Verheyden, P ;

Jaspers, HCM ;

VanBinst, G ;

Tourwe, D .

TETRAHEDRON LETTERS, 1996, 37 (05) :703-706

[2]

GANTE J, 1992, PEPTIDES, P605

[3] ON THE DOUBLE-BOND ISOSTERE OF THE PEPTIDE-BOND - PREPARATION OF AN ENKEPHALIN ANALOG [J].

HANN, MM ;

SAMMES, PG ;

KENNEWELL, PD ;

TAYLOR, JB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (01) :307-314

[4] Novel synthesis of a Phe-Gly E-alkene dipeptide isostere [J].

Kranz, M ;

Kessler, H .

TETRAHEDRON LETTERS, 1996, 37 (30) :5359-5362

[5]

LYGO B, 1992, SYNLETT, P793

[6] REVERSED-PHASE LIQUID-CHROMATOGRAPHIC RESOLUTION OF AMINO-ACID ENANTIOMERS BY DERIVATIZATION WITH 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL ISOTHIOCYANATE [J].

NIMURA, N ;

OGURA, H ;

KINOSHITA, T .

JOURNAL OF CHROMATOGRAPHY, 1980, 202 (03) :375-379

[7] NEW APPROACHES TO THE SYNTHESIS OF TRANS-ALKENE ISOSTERES OF DIPEPTIDES [J].

SPALTENSTEIN, A ;

CARPINO, PA ;

MIYAKE, F ;

HOPKINS, PB .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (17) :3759-3766

[8]

Spatola A. F., 1983, CHEM BIOCH AMINO ACI, V7, P267

[9] Reactions of N-arylsulfonyl-2,3-cis- and N-arylsulfonyl-2,3-trans-3-alkyl-2-vinylaziridines with organocopper reagents:: Importance of 2,3-cis-stereochemistry in controlling regio- and stereoselectivity [J].

Toda, A ;

Aoyama, H ;

Mimura, N ;

Ohno, H ;

Fujii, N ;

Ibuka, T .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (20) :7053-7061

[10]

TODA A, 1997, J AM CHEM SOC, V119, P6040

← 1 2 →