THE STEREOSELECTIVE SYNTHESIS OF (E)-ALKENE DIPEPTIDE ISOSTERES

被引：18

作者：

YONG, YF ^{[1
]}

LIPTON, MA ^{[1
]}

机构：

[1] PURDUE UNIV,DEPT CHEM,W LAFAYETTE,IN 47907

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1993年 / 3卷 / 12期

关键词：

D O I：

10.1016/S0960-894X(01)80783-6

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A diastereo- and enantio- selective synthesis of the (E)-alkene dipeptide isostere of L-Ala-L-Ala from L-alanine has been developed which proceeds via stereocontrolled addition of a (Z)-vinyllithium reagent followed by a [2,3]-Wittig rearrangement. The synthesis proceeds in seven steps overall from L-alanine methyl ester. It is believed that this approach will provide a fairly general and convenient route to isosteres of a number of different dipeptides.

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页码：2879 / 2882

页数：4

相关论文

共 39 条

[1] SYNTHESIS OF ANALOGS OF GABA .14. SYNTHESIS AND ACTIVITY OF UNSATURATED DERIVATIVES OF 5-AMINOPENTANOIC ACID (DELTA-AMINOVALERIC ACID) [J].

ALLAN, RD ;

DICKENSON, HW ;

JOHNSTON, GAR ;

KAZLAUSKAS, R ;

TRAN, HW .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1985, 38 (11) :1651-1656

[2] FLUOROOLEFIN DIPEPTIDE ISOSTERES .1. THE SYNTHESIS OF GLY-PSI(CF=CH)GLY AND RACEMIC PHE-PSI(CF=CH)GLY [J].

ALLMENDINGER, T ;

FURET, P ;

HUNGERBUHLER, E .

TETRAHEDRON LETTERS, 1990, 31 (50) :7297-7300

[3] FLUOROOLEFIN DIPEPTIDE ISOSTERES .2. ENANTIOSELECTIVE SYNTHESIS OF BOTH ANTIPODES OF THE PHE-GLY DIPEPTIDE MIMIC [J].

ALLMENDINGER, T ;

FELDER, E ;

HUNGERBUHLER, E .

TETRAHEDRON LETTERS, 1990, 31 (50) :7301-7304

[4]

BOHNSTEDT AC, 1993, 206TH NAT M AM CHEM

[5] SYNTHESIS OF ALKENE DIPEPTIDE ISOSTERES EMPLOYING THE WITTIG-STILL REARRANGEMENT [J].

BOL, KM ;

LISKAMP, RMJ .

TETRAHEDRON LETTERS, 1991, 32 (39) :5401-5404

[6] SYNTHESIS OF ALKENE DIPEPTIDE ISOSTERES EMPLOYING THE WITTIG-STILL REARRANGEMENT [J].

BOL, KM ;

LISKAMP, RMJ .

TETRAHEDRON, 1992, 48 (31) :6425-6438

[7] PREPARATION OF PROTECTED TRANS-OLEFINIC DIPEPTIDE ISOSTERES [J].

COX, MT ;

HEATON, DW ;

HORBURY, J .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (17) :799-800

[8] INCORPORATION OF TRANS-OLEFINIC DIPEPTIDE ISOSTERES INTO ENKEPHALIN AND SUBSTANCE-P ANALOGS [J].

COX, MT ;

GORMLEY, JJ ;

HAYWARD, CF ;

PETTER, NN .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (17) :800-802

[9]

DEGAETA LSL, 1989, J ORG CHEM, V54, P4004

[10]

ELSEVIERS M, 1990, PEPTIDES CHEM STRUCT, P198

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