Solid-phase synthesis of 2β-methyl substituted penam derivatives through penicillin sulfoxide rearrangement

被引:15
|
作者
Delpiccolo, CML [1 ]
Mata, EG [1 ]
机构
[1] Univ Nacl Rosario, Fac Ciencias Bioquim & Farmaceut, CONICET, Inst Quim Organ Sintesis, RA-2000 Rosario, Santa Fe, Argentina
关键词
D O I
10.1016/S0957-4166(99)00440-1
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A new, robust protocol for the solid-phase synthesis of 2 beta-methyl substituted penam derivatives is described. This synthetic sequence works reliably in good to high overall yields using Merrifield resin as support. The key step involves the thermal rearrangement of the corresponding penicillin sulfoxide. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3893 / 3897
页数:5
相关论文
共 50 条
  • [31] A novel strategy for the solid-phase synthesis of substituted indolines
    Nicolaou, KC
    Roecker, AJ
    Pfefferkorn, JA
    Cao, GQ
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (12) : 2966 - 2967
  • [32] Novel strategy for the solid-phase synthesis of substituted indolines
    Nicolaou, K.C.
    Roecker, A.J.
    Pfefferkorn, Jeffrey A.
    Cao, Gou-Qiang
    1600, ACS, Washington, DC, USA (122):
  • [33] Solid-phase synthesis of substituted quinone compounds.
    Estrada, AY
    Li, QY
    Martinez, LE
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U310 - U310
  • [34] Solid-phase synthesis of N,N′ substituted guanidines
    Dodd, DS
    Wallace, OB
    TETRAHEDRON LETTERS, 1998, 39 (32) : 5701 - 5704
  • [35] Solid-phase synthesis of N,N′-substituted acylguanidines
    Dodd, DS
    Zhao, Y
    TETRAHEDRON LETTERS, 2001, 42 (07) : 1259 - 1262
  • [36] Solid-phase synthesis of 4-substituted quinazolines
    Matlamela, Lerato N.
    Bose, Nripendra K.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
  • [37] Solid-phase synthesis of α-substituted proline hydantoins and analogs
    Alsina, J
    Scott, WL
    O'Donnell, MJ
    TETRAHEDRON LETTERS, 2005, 46 (17) : 3131 - 3135
  • [38] SOLID-PHASE SYNTHESIS OF OLIGONUCLEOSIDE METHYL-PHOSPHONATES
    REDDY, MP
    MURAKAMI, A
    AGRIS, CH
    GLAVE, SA
    MILLER, PS
    TSO, POP
    BIOCHEMISTRY, 1984, 23 (14) : 3371 - 3372
  • [39] A divergent protocol for solid-phase synthesis of highly substituted Bi-aryl furan derivatives
    Han, YX
    Roy, A
    Giroux, A
    TETRAHEDRON LETTERS, 2000, 41 (29) : 5447 - 5451
  • [40] Solid-phase parallel synthesis of substituted dihydroimidazolyl dihydrobenzimidazol-2-ones
    Acharya, AN
    Ostresh, JM
    Houghten, RA
    TETRAHEDRON, 2002, 58 (11) : 2095 - 2100