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
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