Enantioconservative synthesis and ring closing metathesis of disubstituted dialkenic amides

被引:26
作者
Sauriat-Dorizon, H [1 ]
Guibé, F [1 ]
机构
[1] Univ Paris Sud, Inst Chim Mol Orsay, CNRS, Lab React Organ Select, F-91405 Orsay, France
关键词
lactam; metathesis; peptide analogues;
D O I
10.1016/S0040-4039(98)01432-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Optically pure disubstituted dialkenic amides 2, which are direct precursors of Z-ethylenic pseudopeptides 1, are readily synthesized and then cyclized to lactams 3 in the presence of Grubbs' ruthenium-based metathesis catalysts with total conservation of enantiomeric purity. (C) 1998 Elsevier Science Lid. All rights reserved.
引用
收藏
页码:6711 / 6714
页数:4
相关论文
共 16 条
[1]   IMPROVED STEREOCONTROLLED SYNTHESIS OF THREO PEPTIDYL EPOXIDES [J].
ALBECK, A ;
PERSKY, R .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (03) :653-657
[2]  
Armstrong SK, 1998, J CHEM SOC PERK T 1, P371
[3]   AN ENANTIOSELECTIVE AND HIGHLY CONVERGENT SYNTHESIS OF (+)-IKARUGAMYCIN [J].
BOECKMAN, RK ;
WEIDNER, CH ;
PERNI, RB ;
NAPIER, JJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (20) :8036-8037
[4]  
GARROHELION F, 1996, J CHEM SOC CHEM COMM, P641
[5]   Recent advances in olefin metathesis and its application in organic synthesis [J].
Grubbs, RH ;
Chang, S .
TETRAHEDRON, 1998, 54 (18) :4413-4450
[6]   RING-CLOSING METATHESIS AND RELATED PROCESSES IN ORGANIC-SYNTHESIS [J].
GRUBBS, RH ;
MILLER, SJ ;
FU, GC .
ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (11) :446-452
[7]   A thermodynamic preference of chiral N-methanesulfonyl and N-arenesulfonyl 2,3-cis-3-alkyl-2-vinylaziridines over their 2,3-trans-isomers: Useful palladium(0)-catalyzed equilibration reactions for the synthesis of (E)-alkene dipeptide isosteres [J].
Ibuka, T ;
Mimura, N ;
Aoyama, H ;
Akaji, M ;
Ohno, H ;
Miwa, Y ;
Taga, T ;
Nakai, K ;
Tamamura, H ;
Fujii, N ;
Yamamoto, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (04) :999-1015
[8]   A REVERSIBLE PROTECTING GROUP FOR THE AMIDE BOND IN PEPTIDES - USE IN THE SYNTHESIS OF DIFFICULT SEQUENCES [J].
JOHNSON, T ;
QUIBELL, M ;
OWEN, D ;
SHEPPARD, RC .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (04) :369-372
[9]   Asymmetric C-N bond constructions via crotylsilane addition reactions: A stereocontrolled route to dipeptide isosteres [J].
Masse, CE ;
Knight, BS ;
Stavropoulos, P ;
Panek, JS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (26) :6040-6047
[10]   ASYMMETRIC ALKYLATION OF NORMAL-ACYLSULTAMS - A GENERAL-ROUTE TO ENANTIOMERICALLY PURE, CRYSTALLINE C(ALPHA,ALPHA)-DISUBSTITUTED CARBOXYLIC-ACID DERIVATIVES [J].
OPPOLZER, W ;
MORETTI, R ;
THOMI, S .
TETRAHEDRON LETTERS, 1989, 30 (41) :5603-5606