Recent Advances of 1,3-Dipolar Cycloaddition Chemistry for Alkaloid Synthesis

被引:22
作者
Padwa, Albert [1 ]
Bur, Scott [2 ]
机构
[1] Emory Univ, Dept Chem, 1515 Pierce Dr, Atlanta, GA 30322 USA
[2] Gustavus Adolphus Coll, Dept Chem, St Peter, MN 56082 USA
来源
HETEROCYCLIC CHEMISTRY IN THE 21ST CENTURY: A TRIBUTE TO ALAN KATRITZKY | 2016年 / 119卷
基金
美国国家科学基金会;
关键词
1,3-Dipoles; Alkaloids; Asymmetric synthesis; Azides; Azomethine imines; Azomethine ylides; Carbonyl ylides; Cycloaddition; Mesoionic systems; Nitrile oxides; Nitrones; INTRAMOLECULAR DIELS-ALDER/1,3-DIPOLAR CYCLOADDITION; AROMATIC ERYTHRINA-ALKALOIDS; NITRILE OXIDE CYCLOADDITIONS; POLYKETIDE BUILDING-BLOCKS; CYCLIC AZOMETHINE IMINES; DIPOLAR CYCLOADDITION; CARBONYL YLIDES; ALLYL ALCOHOL; CYCLIZATION/CYCLOADDITION CASCADE; HOMOALLYLIC ALCOHOLS;
D O I
10.1016/bs.aihch.2016.03.005
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of heterocyclic compounds has attracted significant attention for decades. Among the various heterocycles isolated from nature, alkaloidal natural products have received significant attention due to their diverse bioactivity. As highlighted in this minireview, a growing area of interest in organic synthesis involves the use of substituted 1,3-dipoles for the preparation of different alkaloidal natural products. Cascade reactions proceeding by an intramolecular 1,3-dipolar cycloaddition chemistry are of particular interest to the synthetic organic community because of the increase in molecular complexity involved and the high isolated yields. The synthesis of numerous alkaloids has been elegantly accomplished in recent years using an assortment of synthetic dipole intermediates.
引用
收藏
页码:241 / 305
页数:65
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