Diastereoselective synthesis of ψ[(E)-CH=CMe]- and ψ[(Z)-CH=CMe]-type dipeptide isosteres by organocopper-mediated anti-SN2′ reaction

被引：16

作者：

Oishi, S

Kamano, T

Niida, A

Odagaki, Y

Tamamura, H

Otaka, A

Hamanaka, N

Fujii, N ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

[2] Ono Pharmaceut Co Ltd, Minase Res Inst, Osaka 6188585, Japan

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 07期

关键词：

D O I：

10.1021/ol016834j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Acyclic Psi[(E)-CH=CMe]- and Psi[(2)-CH Me]-type dipeptide isosteres were efficiently synthesized. In a key reaction, alpha-alkylation of gamma-mesyloxy,beta-methyl-alpha,beta-unsaturated esters with organocyanocuprates in diethyl ether or tetrahydrofuran preferentially afforded the V[(E)-CH=CMe]- or Psi[(2)-CH=CMe]-isomer, respectively, via anti-S(N)2' mechanism.

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收藏

页码：1051 / 1054

页数：4

相关论文

共 28 条

[1] FLUOROALKENES AS PEPTIDE ISOSTERES - GROUND-STATE ANALOG INHIBITORS OF THERMOLYSIN [J].

BARTLETT, PA ;

OTAKE, A .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (10) :3107-3111

[2] Versatile and stereoselective synthesis of diamino diol dipeptide isosteres, core units of pseudopeptide HIV protease inhibitors [J].

Benedetti, F ;

Miertus, S ;

Norbedo, S ;

Tossi, A ;

Zlatoidzky, P .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (26) :9348-9353

[3] A CONCISE ENANTIOSELECTIVE SYNTHESIS OF TRANS-OLEFIN DIPEPTIDE ISOSTERES [J].

BERESIS, R ;

PANEK, JS .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (08) :1609-1614

[4] STABLE ISOSTERES OF NEUROTENSIN C-TERMINAL PENTAPEPTIDES DERIVED BY MODIFICATION OF THE AMIDE FUNCTION [J].

CHRISTOS, TE ;

ARVANITIS, A ;

CAIN, GA ;

JOHNSON, AL ;

POTTORF, RS ;

TAM, SW ;

SCHMIDT, WK .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (06) :1035-1040

[5] N-methylated cyclic RGD peptides as highly active and selective αvβ3 integrin antagonists [J].

Dechantsreiter, MA ;

Planker, E ;

Mathä, B ;

Lohof, E ;

Hölzemann, G ;

Jonczyk, A ;

Goodman, SL ;

Kessler, H .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (16) :3033-3040

[6] S(N)2' RING-OPENING OF AZIRIDINES BEARING AN ALPHA,BETA-UNSATURATED ESTER GROUP WITH ORGANOCOPPER REAGENTS - A NEW STEREOSELECTIVE SYNTHETIC ROUTE TO (E)-ALKENE DIPEPTIDE ISOSTERES [J].

FUJII, N ;

NAKAI, K ;

TAMAMURA, H ;

OTAKA, A ;

MIMURA, N ;

MIWA, Y ;

TAGA, T ;

YAMAMOTO, Y ;

IBUKA, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (11) :1359-1371

[7]

Fujimoto Koji, 1997, Life Sciences, V60, P29

[8] AN ACHIRAL DIPEPTIDE MIMETIC THAT PROMOTES BETA-HAIRPIN FORMATION [J].

GARDNER, RR ;

LIANG, GB ;

GELLMAN, SH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (11) :3280-3281

[9]

Haubner R., 1997, ANGEW CHEM INT EDIT, V36, P1374

[10] Conformational and topographical considerations in designing agonist peptidomimetics from peptide leads [J].

Hruby, VJ ;

Balse, PM .

CURRENT MEDICINAL CHEMISTRY, 2000, 7 (09) :945-970