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
  • [1] Solid-phase organic chemistry:: Synthesis of 2β-(heterocyclylthiomethyl)penam derivatives on solid support
    Delpiccolo, CML
    Mata, EG
    MOLECULES, 2000, 5 (03) : 537 - 538
  • [2] A versatile strategy for the solid-phase synthesis of penicillin derivatives:: Efficient preparation of 2β-methyl substituted penams as β-lactamase inhibitor analogues
    Boggian, Dora B.
    Mata, Ernesto G.
    SYNTHESIS-STUTTGART, 2006, (20): : 3397 - 3404
  • [3] Solid-phase synthesis of substituted 2-aminomethylbenzimidazoles
    Kilburn, JP
    Lau, J
    Jones, RCF
    TETRAHEDRON LETTERS, 2000, 41 (28) : 5419 - 5421
  • [4] Solid-phase synthesis of substituted benzimidazoles
    Tumelty, D
    Schwarz, MK
    Cao, K
    Needels, MC
    TETRAHEDRON LETTERS, 1999, 40 (34) : 6185 - 6188
  • [5] Solid-phase synthesis of dehydroalanine derivatives
    Yamada, M
    Miyajima, T
    Horikawa, H
    TETRAHEDRON LETTERS, 1998, 39 (3-4) : 289 - 292
  • [6] Solid-phase Synthesis of Phosphorus Derivatives
    Simulescu, Vasile
    Ilia, Gheorghe
    CURRENT ORGANIC CHEMISTRY, 2019, 23 (06) : 679 - 688
  • [7] Divergent protocol for solid-phase synthesis of highly substituted furan derivatives.
    Han, YX
    Roy, A
    Giroux, A
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U127 - U127
  • [8] Solid-Phase Synthesis of N-Substituted Glycine Oligomers (α-Peptoids) and Derivatives
    Culf, Adrian S.
    Ouellette, Rodney J.
    MOLECULES, 2010, 15 (08) : 5282 - 5335
  • [9] Solid-phase synthesis of N-substituted amidinoaryloxy pyridine derivatives.
    Mohan, R
    Buckman, BO
    Yun, W
    Liang, A
    Trinh, L
    Morrissey, MM
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 215 : U899 - U899
  • [10] Traceless solid-phase synthesis of substituted xanthines
    He, Rongjun
    Ching, Shi Min
    Lam, Yulin
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2006, 8 (06): : 923 - 928