Asymmetric total synthesis of natural diheteropeptin

被引:4
作者
Durand, P [1 ]
Peralba, P [1 ]
Derain, V [1 ]
Komesli, S [1 ]
Renaut, P [1 ]
机构
[1] Lab Fournier SA, F-21121 Daix, France
关键词
asymmetric dihydroxylation; amino acid synthesis; diheteropeptin; cyclic peptide;
D O I
10.1016/S0040-4039(01)00139-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A total asymmetric synthesis of diheteropeptin and a stereomer from the known (E)-1-iodo-6-octene, using the Schollkopf method for amino acid synthesis and Sharpless asymmetric dihydroxylation as key steps, is described. The asymmetric synthesis of a new unsaturated amino acid is also described. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2121 / 2124
页数:4
相关论文
共 28 条
[1]   A NEW HOMOLYTIC METHOD FOR THE STEREOSPECIFIC SYNTHESIS OF (2S,9S)-2-AMINO-8-OXO-9,10-EPOXYDECANOIC ACID IN PROTECTED FORM [J].
BALDWIN, JE ;
ADLINGTON, RM ;
GODFREY, CRA ;
PATEL, VK .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (18) :1277-1279
[2]   STEREOSPECIFIC SYNTHESIS OF CHLAMYDOCIN [J].
BALDWIN, JE ;
ADLINGTON, RM ;
GODFREY, CRA ;
PATEL, VK .
TETRAHEDRON, 1993, 49 (36) :7837-7856
[3]  
BERNARDI E, 1994, B SOC CHIM FR, V131, P944
[4]   Mechanisms of disease:: Role of transforming growth factor β in human disease. [J].
Blobe, GC ;
Schiemann, WP ;
Lodish, HF .
NEW ENGLAND JOURNAL OF MEDICINE, 2000, 342 (18) :1350-1358
[5]   Transforming growth factor-beta (TGF-β) [J].
Clark, DA ;
Coker, R .
INTERNATIONAL JOURNAL OF BIOCHEMISTRY & CELL BIOLOGY, 1998, 30 (03) :293-298
[6]   ISOLATION AND STRUCTURAL ELUCIDATION OF CHLAMYDOCIN [J].
CLOSSE, A ;
HUGUENIN, R .
HELVETICA CHIMICA ACTA, 1974, 57 (03) :533-545
[7]   PYBOP - A NEW PEPTIDE COUPLING REAGENT DEVOID OF TOXIC BY-PRODUCT [J].
COSTE, J ;
LENGUYEN, D ;
CASTRO, B .
TETRAHEDRON LETTERS, 1990, 31 (02) :205-208
[8]   ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].
DALE, JA ;
DULL, DL ;
MOSHER, HS .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&
[9]  
DEMEDEIROS EF, 1991, J CHEM SOC P1, V11, P2725
[10]  
GRUIEC R, 1994, B SOC CHIM FR, V131, P699