TOTAL SYNTHESIS OF CYCLOTHEONAMIDE-B, A FACILE ROUTE TOWARDS ANALOGS

被引:13
作者
BASTIAANS, HMM
VANDERBAAN, JL
OTTENHEIJM, HCJ
机构
[1] LEIDEN AMSTERDAM CTR DRUG RES,DEPT PHARMACOCHEM,DIV MED CHEM,1081 HV AMSTERDAM,NETHERLANDS
[2] VRIJE UNIV AMSTERDAM,SCHEIKUNDIG LAB,1081 HV AMSTERDAM,NETHERLANDS
[3] NV ORGANON,SCI DEV GRP,5340 BH OSS,NETHERLANDS
关键词
D O I
10.1016/0040-4039(95)01153-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A flexible, convergent synthesis of Cyclotheonamide B (1b) was developed, starting from the constituent amino acids, using conventional benzyl-, t-butyl- and allyl-based protecting groups. By modification of the key intermediates, this approach allows the preparation of cyclotheonamide analogues.
引用
收藏
页码:5963 / 5966
页数:4
相关论文
共 15 条
  • [1] DENG J, 1994, ANGEW CHEM, V106, P1811
  • [2] A SELECTIVE PROTECTION OF 2,3-DIAMINOPROPIONIC ACID
    EGBERTSON, MS
    HOMNICK, CF
    HARTMAN, GD
    [J]. SYNTHETIC COMMUNICATIONS, 1993, 23 (05) : 703 - 709
  • [3] BIOACTIVE MARINE METABOLITES .33. CYCLOTHEONAMIDES, POTENT THROMBIN INHIBITORS, FROM A MARINE SPONGE THEONELLA SP
    FUSETANI, N
    MATSUNAGA, S
    MATSUMOTO, H
    TAKEBAYASHI, Y
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (19) : 7053 - 7054
  • [4] SELECTIVE REMOVAL OF AN N-BOC PROTECTING GROUP IN THE PRESENCE OF A TERT-BUTYL ESTER AND OTHER ACID-SENSITIVE GROUPS
    GIBSON, FS
    BERGMEIER, SC
    RAPOPORT, H
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (11) : 3216 - 3218
  • [5] REASSIGNMENT OF STEREOCHEMISTRY AND TOTAL SYNTHESIS OF THE THROMBIN INHIBITOR CYCLOTHEONAMIDE-B
    HAGIHARA, M
    SCHREIBER, SL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (16) : 6570 - 6571
  • [6] ATOMIC-STRUCTURE OF THE TRYPSIN CYCLOTHEONAMIDE A COMPLEX - LESSONS FOR THE DESIGN OF SERINE-PROTEASE INHIBITORS
    LEE, AY
    HAGIHARA, M
    KARMACHARYA, R
    ALBERS, MW
    SCHREIBER, SL
    CLARDY, J
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (26) : 12619 - 12620
  • [7] INHIBITION OF THROMBIN AND OTHER TRYPSIN-LIKE SERINE PROTEINASES BY CYCLOTHEONAMIDE-A
    LEWIS, SD
    NG, AS
    BALDWIN, JJ
    FUSETANI, N
    NAYLOR, AM
    SHAFER, JA
    [J]. THROMBOSIS RESEARCH, 1993, 70 (02) : 173 - 190
  • [8] LIN ZL, 1994, PROTEIN PEPTIDE LETT, V1, P9
  • [9] MACROCYCLIC PEPTIDE INHIBITORS OF SERINE PROTEASES - CONVERGENT TOTAL SYNTHESIS OF CYCLOTHEONAMIDE-A AND CYCLOTHEONAMIDE-B VIA A LATE-STAGE PRIMARY AMINE INTERMEDIATE - STUDY OF THROMBIN INHIBITION UNDER DIVERSE CONDITIONS
    MARYANOFF, BE
    GRECO, MN
    ZHANG, HC
    ANDRADEGORDON, P
    KAUFFMAN, JA
    NICOLAOU, KC
    LIU, AJ
    BRUNGS, PH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (04) : 1225 - 1239
  • [10] MOLECULAR-BASIS FOR THE INHIBITION OF HUMAN ALPHA-THROMBIN BY THE MACROCYCLIC PEPTIDE CYCLOTHEONAMIDE-A
    MARYANOFF, BE
    QIU, XY
    PADMANABHAN, KP
    TULINSKY, A
    ALMOND, HR
    ANDRADEGORDON, P
    GRECO, MN
    KAUFFMAN, JA
    NICOLAOU, KC
    LIU, AJ
    BRUNGS, PH
    FUSETANI, N
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1993, 90 (17) : 8048 - 8052