Synthesis of partially modified retro and retroinverso ψ[NHCH(CF3)]-peptides

被引：71
作者：
Volonterio, A
Bravo, P
Zanda, M
机构：
[1] Politecn Milan, Dipartimento Chim, I-20131 Milan, Italy
[2] CNR, Ctr Studio Sostanze Organ Nat, I-20131 Milan, Italy
来源：
ORGANIC LETTERS | 2000年 / 2卷 / 13期
关键词：
D O I：
10.1021/ol005876p
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Asymmetric conjugate additions of chiral alpha-amino esters to chiral 4-CF3 Michael-acceptors were exploited to prepare a small library of enantiomerically pure partially modified retropeptides having a psi[NHCH(CF3)] unit as a possible mimic of the classical psi(NHCO) retropeptide unit. Yields were nearly quantitative, and the stereoselectivity, which is controlled mainly by the nitrogen nucleophile, was progressively higher with increasing the steric bulk of the alpha-amino ester side-chain R-1.
引用
收藏
页码：1827 / 1830
页数：4
相关论文
共 43 条
[21]  
GANTE J, 1994, ANGEW CHEM INT EDIT, V33, P1699, DOI 10.1002/anie.199416991
[22]   Synthesis of potent and selective inhibitors of human plasma kallikrein [J].
Garrett, GS ;
McPhail, SJ ;
Tornheim, K ;
Correa, PE ;
McIver, JM .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (03) :301-306
[23]   CONCEPT OF LINEAR MODIFIED RETRO-PEPTIDE STRUCTURES [J].
GOODMAN, M ;
CHOREV, M .
ACCOUNTS OF CHEMICAL RESEARCH, 1979, 12 (01) :1-7
[24]   ASYMMETRIC-SYNTHESIS OF ERYTHRO AND THREO ALPHA-SUBSTITUTED BETA-AMINO ESTERS [J].
HAWKINS, JM ;
LEWIS, TA .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (03) :649-652
[25]   ASYMMETRIC MICHAEL REACTIONS OF 3,5-DIHYDRO-4H-DINAPHTH[2,1-C-1',2'-E]AZEPINE WITH METHYL CROTONATE [J].
HAWKINS, JM ;
FU, GC .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (14) :2820-2822
[26]   Pseudopeptide CCK-4 analogues incorporating the Psi[CH(CN)NH] peptide bond surrogate [J].
Herrero, S ;
SuarezGea, ML ;
GonzalezMuniz, R ;
GarciaLopez, MT .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (07) :855-860
[27]   CARBAMATE-MEDIATED FUNCTIONALIZATION OF UNSATURATED ALCOHOLS .3. INTRAMOLECULAR MICHAEL ADDITION OF O-CARBAMATES TO ALPHA,BETA-UNSATURATED ESTERS - A NEW DIASTEREOSELECTIVE AMINATION IN AN ACYCLIC SYSTEM [J].
HIRAMA, M ;
SHIGEMOTO, T ;
YAMAZAKI, Y ;
ITO, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (06) :1797-1798
[28]   A stereocontrolled synthesis of monofluoro ketomethylene dipeptide isosteres [J].
Hoffman, RV ;
Tao, JH .
TETRAHEDRON LETTERS, 1998, 39 (24) :4195-4198
[29]   Protease inhibitors: Current status and future prospects [J].
Leung, D ;
Abbenante, G ;
Fairlie, DP .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (03) :305-341
[30]   STEREOSELECTIVE CONJUGATE ADDITION-ALKYLATIONS OF ALPHA,BETA-UNSATURATED IRON ACYLS [J].
LIEBESKIND, LS ;
WELKER, ME .
TETRAHEDRON LETTERS, 1985, 26 (26) :3079-3082
12345