Creation of quarternary stereocentres via [3,3]-sigmatropic rearrangement of allylic thiocyanates.: A synthetic approach to (+)-myriocin

被引：35
|
作者：
Gonda, Jozef [1 ]
Martinkova, Miroslava [1 ]
Raschmanova, Jana [1 ]
Balentova, Eva [1 ]
机构：
[1] Safarik Univ, Dept Organ Chem, Inst Chem, SK-04001 Kosice, Slovakia
来源：
TETRAHEDRON-ASYMMETRY | 2006年 / 17卷 / 12期
关键词：
D O I：
10.1016/j.tetasy.2006.06.032
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
A stereoselective approach to the advanced precursor of (+)-myriocin, 3-deoxy-1,2:5,6-di-O-isopropylidene-3-methoxycarbonylamino-alpha-D-glucofuranose 3-C-carboxylic acid, via the [3,3]-sigmatropic rearrangement of allylic thiocyanates prepared from D-glucose is presented. From the observed results, supported by DFT calculations, we can conclude that the [3,3]-sigmatropic rearrangement of the thiocyanato group in allylic hexofuranosides is strongly influenced by the steric interaction of the 1,2-O-isopropylidene group in the transition states. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1875 / 1882
页数：8
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