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

页码：89 / 96

页数：8

共 28 条

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[6] Catalytic Enantioselective 1,3-Dipolar Cycloaddition of C,N-Cyclic Azomethine Imines with α,β-Unsaturated Aldehydes
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[8] Synthesis of Constrained C-Glycosyl Amino Acid Derivatives Involving 1,3-Dipolar Cycloaddition of Cyclic Nitrone as Key Step
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[9] A theoretical study of the mechanism and selectivity of the intramolecular 1,3-dipolar cycloaddition reaction of the nitrone-alkene derived from 2-allylthiobenzaldehyde for the synthesis of tricyclic isoxazolidines
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