Selective photochemical cleavage of an α-ketoamide in a highly functionalised macrolide ascomycin

被引:4
作者
Bulusu, MARC [1 ]
Waldstätten, P [1 ]
Tricotett, T [1 ]
Schulz, G [1 ]
机构
[1] Novartis Inst Biomed Res, A-1235 Vienna, Austria
关键词
phototransformation; photochemical amide cleavage; zwitterion;
D O I
10.1016/j.tetlet.2004.02.014
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel photochemical amide cleavage reaction of (6S)-methoxyascomycin opening a pathway for the selective cleavage of the pipecolic acid, is described. The scope of this reaction with several analogues carrying suitable protecting groups is examined. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2527 / 2530
页数:4
相关论文
共 27 条
  • [21] IDENTITY OF IMMUNOSUPPRESSANT FR-900520 WITH ASCOMYCIN
    MORISAKI, M
    ARAI, T
    [J]. JOURNAL OF ANTIBIOTICS, 1992, 45 (01) : 126 - 128
  • [22] SYNTHETIC METHODS AND REACTIONS .62. TRANSFORMATIONS WITH CHLOROTRIMETHYLSILANE SODIUM IODIDE, A CONVENIENT IN SITU IODOTRIMETHYLSILANE REAGENT
    OLAH, GA
    NARANG, SC
    GUPTA, BGB
    MALHOTRA, R
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (08) : 1247 - 1251
  • [23] Pimecrolimus identifies a common genomic anti-inflammatory profile, is clinically highly effective in psoriasis and is well tolerated
    Rappersberger, K
    Komar, M
    Ebelin, ME
    Scott, G
    Burtin, P
    Greig, G
    Kehren, J
    Chibout, SD
    Cordier, A
    Holter, W
    Richter, L
    Oberbauer, R
    Stuetz, A
    Wolff, K
    [J]. JOURNAL OF INVESTIGATIVE DERMATOLOGY, 2002, 119 (04) : 876 - 887
  • [24] Pimecrolimus (Elidel, SDZ ASM 981) - Preclinical pharmacologic profile and skin selectivity
    Stuetz, A
    Grassberger, M
    Meingassner, JG
    [J]. SEMINARS IN CUTANEOUS MEDICINE AND SURGERY, 2001, 20 (04) : 233 - 241
  • [25] ATOMIC-STRUCTURE OF FKBP-FK506, AN IMMUNOPHILIN-IMMUNOSUPPRESSANT COMPLEX
    VANDUYNE, GD
    STANDAERT, RF
    KARPLUS, PA
    SCHREIBER, SL
    CLARDY, J
    [J]. SCIENCE, 1991, 252 (5007) : 839 - 842
  • [26] Efficacy and safety of pimecrolimus cream in the long-term management of atopic dermatitis in children
    Wahn, U
    Bos, JD
    Goodfield, M
    Caputo, R
    Papp, K
    Manjra, A
    Dobozy, A
    Paul, C
    Molloy, S
    Hultsch, T
    Graeber, M
    Cherill, R
    de Prost, Y
    [J]. PEDIATRICS, 2002, 110 (01) : e2
  • [27] Topical pimecrolimus - A review of its clinical potential in the management of atopic dermatitis
    Wellington, K
    Jarvis, B
    [J]. DRUGS, 2002, 62 (05) : 817 - 840