Asymmetric synthesis of (3S,4R,5R)-4,5-dihydroxy-3-methyl-2,3,4,5-tetrahydropyridazine:: a formal synthesis of 1-azagulofagomine analogues

被引：21
|
作者：
Arroyo, Y
Rodríguez, JF
Santos, M
Tejedor, MAS
Vaca, I
Ruano, JLG
机构：
[1] Univ Valladolid, Dept Organ Chem, E-47011 Valladolid, Spain
[2] Univ Autonoma Madrid, Dept Organ Chem, E-28049 Madrid, Spain
来源：
TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 06期
关键词：
D O I：
10.1016/j.tetasy.2004.01.037
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The stereoselective synthesis of (3S,4R,5R)-4,5-dihydroxy-3-methyl-2,3,4,5-tetrahydropyridazine from [(S)R]-(1E,3E)-1-p-tolylsulfinyl-1,3-pentadiene is reported. The domino reaction of the 1-sulfinyldiene with 1,2,4-triazoline-3,5-dione (a hetero Diels-Alder, sulfoxide-sulfenate rearrangement, and sulfenate hydrolysis), eis-dihydroxylation of the resulting alkene and hydrazinolysis with elimination of a N-methylurazol residue are the key steps of the sequence. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1059 / 1063
页数：5
相关论文
共 50 条
  • [31] IMPROVED SYNTHESIS OF (2R,3S,4R)-3,4-DIHYDROXY-2-HYDROXYMETHYL-PYRROLIDINE DERIVATIVES
    IKOTA, N
    HANAKI, A
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1988, 36 (03) : 1143 - 1146
  • [32] Chemoenzymatic synthesis of orthogonally protected (3R,4R)- and (3S,4S)-trans-3-amino-4-hydroxypyrrolidines
    Rodriguez-Rodriguez, Jesus A.
    Javier Quijada, F.
    Brieva, Rosario
    Rebolledo, Francisca
    Gotor, Vicente
    TETRAHEDRON, 2013, 69 (26) : 5407 - 5412
  • [33] Synthesis of three branched iminosugars [(3R,4R,5S)-3-(hydroxymethyl)piperidine-3,4,5-triol, (3R,4R,5R)-3-(hydroxymethyl)piperidine-3,4,5-triol and (3S,4R,5R)-3-(hydroxymethyl)piperidine-3.4,5-triol] and a branched trihydroxynipecotic acid [(3R,4R,5R)-3,4,5-trihydroxypiperidine-3-carboxylic acid] from sugar lactones with a carbon substituent at C-2
    Simone, Michela I.
    Soengas, Raquel G.
    Jenkinson, Sarah F.
    Evinson, Emma L.
    Nash, Robert J.
    Fleet, George W. J.
    TETRAHEDRON-ASYMMETRY, 2012, 23 (05) : 401 - 408
  • [34] SYNTHESIS OF (3S,4S)-4-HYDROXY-2,3,4,5-TETRAHYDROPYRIDAZINE-3-CARBOXYLIC ACID, COMPONENT OF LUZOPEPTIN-A
    GRECK, C
    BISCHOFF, L
    GENET, JP
    TETRAHEDRON-ASYMMETRY, 1995, 6 (08) : 1989 - 1994
  • [35] SHORT SYNTHESIS OF (3S,4R)-3-HYDROXY-4-HYDROXYMETHYL-4-BUTANOLIDE AND (3R,4R)-3-HYDROXY-4-HYDROXYMETHYL-4-BUTANOLIDE, 2 LACTONES FROM LEVOGLUCOSENONE
    MATSUMOTO, K
    EBATA, T
    KOSEKI, K
    OKANO, K
    KAWAKAMI, H
    MATSUSHITA, H
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1995, 68 (02) : 670 - 672
  • [36] An efficient synthesis of an optically active (-)-(3R, 4R, 5R)-4-(1-hydroxylisopropyl)-3-acetyloxyl-butyrolactone
    Wang, JX
    Zhang, CX
    Li, Y
    You, QD
    JOURNAL OF CHEMICAL RESEARCH-S, 2005, (10): : 665 - 668
  • [37] WORKSPACE SYNTHESIS OF 3R, 4R, 5R AND 6R ROBOTS.
    Tsai, Y.C.
    Soni, A.H.
    1600, (20):
  • [38] PHEROMONE SYNTHESIS .68. SYNTHESIS OF (3S,4S)-4-METHYL-3-HEPTANOL AND ITS (3S,4R)-ISOMER EMPLOYING ASYMMETRIC EPOXIDATION COUPLED WITH REGIOSELECTIVE CLEAVAGE OF EPOXIDES WITH TRIMETHYLALUMINUM
    NAKAGAWA, N
    MORI, K
    AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1984, 48 (10): : 2505 - 2510
  • [39] Total synthesis of (2S,3S,4R)-plakoridine A
    Ma, DW
    Sun, HY
    TETRAHEDRON LETTERS, 2000, 41 (12) : 1947 - 1950
  • [40] Short and efficient synthesis of (2S,3R,4R,5R) and (2S,3R,4R,5S)-tetrahydroxyazepanes via the Henry reaction
    Chakraborty, C
    Dhavale, DD
    CARBOHYDRATE RESEARCH, 2006, 341 (07) : 912 - 917
12345