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

页码：1059 / 1063

页数：5

共 38 条

[1]

[Anonymous], 1994, ANGEW CHEM, V106, P1858

[2] FIRST DIELS-ALDER REACTIONS OF ENANTIOMERICALLY PURE 1-P-TOLYLSULFINYL DIENES - STRAIGHTFORWARD ACCESS TO CYCLOHEXENOLS THROUGH TANDEM CYCLOADDITION [2,3]-SIGMATROPIC REARRANGEMENT [J].