SYNTHESIS OF ALKENE DIPEPTIDE ISOSTERES EMPLOYING THE WITTIG-STILL REARRANGEMENT

被引:19
作者
BOL, KM [1 ]
LISKAMP, RMJ [1 ]
机构
[1] LEIDEN UNIV,GORLAEUS LABS,POB 9502,2300 RA LEIDEN,NETHERLANDS
关键词
D O I
10.1016/S0040-4039(00)92397-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new approach to the synthesis of alkene dipeptide isosteres is reported which features the use of the [2,3]-Wittig-Still rearrangement, carried out in hexane. As an example the synthesis of the alkene dipeptide isostere of Gly-Ala as part of the tripeptide isostere Z-Phe-Gly-PSI[E-CH = CH]-(R, S)Ala-OH is described.
引用
收藏
页码:5401 / 5404
页数:4
相关论文
共 38 条
  • [11] SYNTHETIC APPLICATIONS OF TRIMETHYLSILYL CYANIDE - EFFICIENT SYNTHESIS OF BETA-AMINOMETHYL ALCOHOLS
    EVANS, DA
    CARROLL, GL
    TRUESDALE, LK
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (07) : 914 - 917
  • [12] DOUBLE-BOND ISOSTERES OF THE PEPTIDE-BOND - ENKEPHALIN ANALOG
    HANN, MM
    SAMMES, PG
    KENNEWELL, PD
    TAYLOR, JB
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (05) : 234 - 235
  • [13] ON THE DOUBLE-BOND ISOSTERE OF THE PEPTIDE-BOND - PREPARATION OF AN ENKEPHALIN ANALOG
    HANN, MM
    SAMMES, PG
    KENNEWELL, PD
    TAYLOR, JB
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (01): : 307 - 314
  • [14] HIGHLY SELECTIVE SYNTHESIS OF (E)-ALKENE ISOSTERIC DIPEPTIDES WITH HIGH OPTICAL PURITY VIA RCU(CN)LI.BF3 MEDIATED REACTION
    IBUKA, T
    HABASHITA, H
    FUNAKOSHI, S
    FUJII, N
    OGUCHI, Y
    UYEHARA, T
    YAMAMOTO, Y
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (07): : 801 - 803
  • [15] SEQUENCE-SPECIFIC PEPTIDE CLEAVAGE CATALYZED BY AN ANTIBODY
    IVERSON, BL
    LERNER, RA
    [J]. SCIENCE, 1989, 243 (4895) : 1184 - 1188
  • [16] INDUCTION OF AN ANTIBODY THAT CATALYZES THE HYDROLYSIS OF AN AMIDE BOND
    JANDA, KD
    SCHLOEDER, D
    BENKOVIC, SJ
    LERNER, RA
    [J]. SCIENCE, 1988, 241 (4870) : 1188 - 1191
  • [17] JOHNSON RL, 1985, J CHEM SOC P1, P2299
  • [18] RENIN INHIBITORS CONTAINING ISOSTERIC REPLACEMENTS OF THE AMIDE BOND CONNECTING THE P3 AND P2 SITES
    KALTENBRONN, JS
    HUDSPETH, JP
    LUNNEY, EA
    MICHNIEWICZ, BM
    NICOLAIDES, ED
    REPINE, JT
    ROARK, WH
    STIER, MA
    TINNEY, FJ
    WOO, PKW
    ESSENBURG, AD
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (02) : 838 - 845
  • [19] AMINO PROTECTION USING TRIAZONES
    KNAPP, S
    HALE, JJ
    BASTOS, M
    GIBSON, FS
    [J]. TETRAHEDRON LETTERS, 1990, 31 (15) : 2109 - 2112
  • [20] DOES THE WITTIG-STILL REARRANGEMENT PROCEED VIA A METAL FREE CARBANION
    KRUSE, B
    BRUCKNER, R
    [J]. TETRAHEDRON LETTERS, 1990, 31 (31) : 4425 - 4428