The squalestatins:: tricyclic 3,4-β-lactone and 3,4-oxetane systems

被引:1
作者
Cox, B
Morley, N
Procopiou, PA
Sharratt, PJ
Watson, NS
Wild, D
机构
[1] Glaxo Wellcome Res & Dev Ltd, Med Res Ctr, Dept Med Chem 1, Stevenage SG1 2NY, Herts, England
[2] Glaxo Wellcome Res & Dev Ltd, Med Res Ctr, Dept Med Chem 2, Stevenage SG1 2NY, Herts, England
关键词
D O I
10.1016/S0040-4039(00)01286-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Squalestatin 3,4-beta-lactone-4,5-dimethyl ester (8) was reductively ring-opened to yield squalestatin 3-hydroxymethyl-4,5-dimethyl ester (6) using mild reducing conditions (sodium borohydride). Similarly squalestatin 3,4-oxetane-4,5-dimethyl ester (10) was found to ring-open to 3-iodomethyl squalestatin (15) under the conditions used to cleave the methyl ester functions (lithium iodide/2,4,6-trimethylpyridine). (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7547 / 7550
页数:4
相关论文
共 12 条
  • [1] AMOUROUX R, 1987, B SOC CHIM FR, P505
  • [2] BIFTU T, 1994, Patent No. 2275470
  • [3] THE SQUALESTATINS - POTENT INHIBITORS OF SQUALENE SYNTHASE, 3-HYDROXYMETHYL DERIVATIVES
    COX, B
    HUTSON, JL
    KEELING, SE
    KIRK, BE
    SRIKANTHA, ARP
    WATSON, NS
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (16) : 1931 - 1936
  • [4] NOTIZ UBER DIE SELEKTIVITAT DER SPALTUNG VON CARBONSAURE-METHYLESTERN MIT LITHIUMJODID
    ELSINGER, F
    SCHREIBER, J
    ESCHENMOSER, A
    [J]. HELVETICA CHIMICA ACTA, 1960, 43 (01) : 113 - 118
  • [5] CHEMOSELECTIVE REDUCTION OF CARBOXYLIC-ACIDS INTO ALCOHOLS USING N,N-DIMETHYLCHLOROMETHYLENIMINIUM CHLORIDE AND SODIUM-BOROHYDRIDE
    FUJISAWA, T
    MORI, T
    SATO, T
    [J]. CHEMISTRY LETTERS, 1983, (06) : 835 - 838
  • [6] KOLL P, 1987, LIEBIGS ANN CHEM, P205
  • [7] THE SYNTHESIS OF C3-METHYL, C3-DECARBOXY-ZARAGOZIC ACID-A - A POTENT SQUALENE SYNTHASE INHIBITOR
    KUO, CH
    PLEVYAK, SP
    BIFTU, T
    PARSONS, WH
    BERGER, GD
    [J]. TETRAHEDRON LETTERS, 1993, 34 (43) : 6863 - 6866
  • [8] REACTION OF TERT-BUTYLCYANOKETENE WITH TERTIARY-AMINES - SYNTHESIS OF "1,3-DI-TERT-BUTYL-1,3-DICYANOALLENE
    MOORE, HW
    DUNCAN, WG
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (01) : 156 - 158
  • [9] The squalestatins: Inhibitors of squalene synthase. Enzyme inhibitory activities and in vivo evaluation of C3-modified analogues
    Procopiou, PA
    Cox, B
    Kirk, BE
    Lester, MG
    McCarthy, AD
    Sareen, M
    Sharratt, PJ
    Snowden, MA
    Spooner, SJ
    Watson, NS
    Widdowson, J
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (07) : 1413 - 1422
  • [10] SIMPLE ONE-POT METHOD FOR ESTERIFICATION
    STADLER, PA
    [J]. HELVETICA CHIMICA ACTA, 1978, 61 (05) : 1675 - 1681