DIASTEREOSELECTIVE SYNTHESIS OF THE KEY LACTONE INTERMEDIATE FOR THE PREPARATION OF HYDROXYETHYLENE DIPEPTIDE ISOSTERES

被引:28
作者
LAGU, BR [1 ]
LIOTTA, DC [1 ]
机构
[1] EMORY UNIV,DEPT CHEM,ATLANTA,GA 30322
关键词
D O I
10.1016/S0040-4039(00)75834-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient and highly stereoselective route for preparing hydroxyethylene dipeptide isosteres from alpha-N,N-dibenzylamino ketones has been developed.
引用
收藏
页码:547 / 550
页数:4
相关论文
共 16 条
[1]   ONE-POT TRANSFORMATION OF BENZYL CARBAMATES INTO TERT-BUTYL CARBAMATES [J].
BAJWA, JS .
TETRAHEDRON LETTERS, 1992, 33 (21) :2955-2956
[2]  
BASHA A, 1977, TETRAHEDRON LETT, V18, P4171, DOI DOI 10.1016/S0040-4039(01)83457-2
[3]   STEREOCONTROLLED ADDITION OF PROPIONATE HOMOENOLATE EQUIVALENTS TO CHIRAL ALPHA-AMINO ALDEHYDES [J].
DECAMP, AE ;
KAWAGUCHI, AT ;
VOLANTE, RP ;
SHINKAI, I .
TETRAHEDRON LETTERS, 1991, 32 (16) :1867-1870
[4]   STEREOSELECTIVE SYNTHESIS OF A HYDROXYETHYLENE DIPEPTIDE ISOSTERE [J].
DIEDERICH, AM ;
RYCKMAN, DM .
TETRAHEDRON LETTERS, 1993, 34 (39) :6169-6172
[5]   HOMOLOGATION OF L-PHENYLALANINE TO KETOMETHYLENE AND HYDROXYETHYLENE DIPEPTIDE ISOSTERES VIA 2-THIAZOLYL AMINO KETONE INTERMEDIATE [J].
DONDONI, A ;
PERRONE, D .
TETRAHEDRON LETTERS, 1992, 33 (47) :7259-7262
[6]   A STEREOCONTROLLED SYNTHESIS OF HYDROXYETHYLENE DIPEPTIDE ISOSTERES USING NOVEL, CHIRAL AMINOALKYL EPOXIDES AND GAMMA-(AMINOALKYL) GAMMA-LACTONES [J].
EVANS, BE ;
RITTLE, KE ;
HOMNICK, CF ;
SPRINGER, JP ;
HIRSHFIELD, J ;
VEBER, DF .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (23) :4615-4625
[7]   A SHORT, STEREOSELECTIVE SYNTHESIS OF THE LACTONE PRECURSOR TO 2R,4S,5S HYDROXYETHYLENE DIPEPTIDE ISOSTERES [J].
FRAY, AH ;
KAYE, RL ;
KLEINMAN, EF .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (25) :4828-4833
[8]   AN EFFICIENT SYNTHESIS OF HYDROXYETHYLENE DIPEPTIDE ISOSTERES - THE CORE UNIT OF POTENT HIV-1 PROTEASE INHIBITORS [J].
GHOSH, AK ;
MCKEE, SP ;
THOMPSON, WJ .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (23) :6500-6503
[9]   A SIMPLE SYNTHETIC APPROACH TO CBZ-PHE-PSI-(CH2)GLY-PRO-OME AND RELATED PEPTIDE ISOSTERES [J].
HOFFMAN, RV ;
KIM, HO .
TETRAHEDRON LETTERS, 1992, 33 (25) :3579-3582
[10]   HIGHLY DIASTEREOSELECTIVE ALDOL REACTIONS OF CHIRAL METHYL KETONES [J].
LAGU, BR ;
CRANE, HM ;
LIOTTA, DC .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (16) :4191-4193