1,3-Dipolar cycloaddition of a cyclic nitrone derived from 2-deoxy-D-ribose to α,β-unsaturated lactones: An entry to carbapenem antibiotics

被引：3
|
作者：
Pieczykolan, Michal [1 ]
Staszewska-Krajewska, Olga [1 ]
Furman, Bartlomiej [1 ]
Chmielewski, Marek [1 ]
机构：
[1] Polish Acad Sci, Inst Organ Chem, Kasprzaka 44-52, PL-01224 Warsaw, Poland
来源：
CARBOHYDRATE RESEARCH | 2016年 / 433卷
关键词：
beta-Lactams; 1,3-Dipolar cycloaddition; Nitrones; gamma- and delta-unsaturated lactones; DOUBLE ASYMMETRIC INDUCTION; 3,4,5,6-TETRAHYDROPYRIDINE 1-OXIDE; ASSIGNMENT; DFT;
D O I：
10.1016/j.carres.2016.07.002
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
1,3-Dipolar cycloadditions of 2-deoxy-D-ribose-derived L-threo five-membered cyclic nitrone to alpha,beta-unsaturated gamma- and delta-lactones were investigated. Cycloadducts obtained from d-lactones, after N-O bond cleavage, opening of the lactone ring, and protection of hydroxyl groups were subjected to beta-lactam ring formation by using Mukaiyama's salt. Cycloadducts from gamma-lactones subjected to the same reaction sequence undergo beta-elimination of a water molecule to provide pyrrolidine-substituted unsaturated gamma-lactones. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：89 / 96
页数：8
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