Synthesis of the Core Ring System of the Yuzurimine-Type Daphniphyllum Alkaloids by Cascade Condensation, Cyclization, Cycloaddition Chemistry

被引:42
|
作者
Coldham, Iain [1 ]
Watson, Luke [1 ]
Adams, Harry [1 ]
Martin, Nathaniel G. [2 ]
机构
[1] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England
[2] AstraZeneca, Macclesfield SK10 4TG, Cheshire, England
来源
JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 07期
基金
英国工程与自然科学研究理事会;
关键词
FUSED TRICYCLIC AMINES; DIPOLAR CYCLOADDITION; BUILDING-BLOCKS; ACYCLIC ALDEHYDES; DAPHNILACTONE-B; HISTRIONICOTOXIN; CONSTRUCTION; TANDEM;
D O I
10.1021/jo2000868
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Addition of hydroxylamine to substituted 4-cblorobutanals gives intermediate nitrones that undergo tandem cyclization and then intramolecular dipolar cycloaddition to give the core ring system of the yuzurimine-type natural products. Ring-opening of the isoxazolidines gives amino alcohols that can be converted to 1,3-oxazines, representing the tetracyclic core of alkaloids such as daphcalycic acid and daphcalycine.
引用
收藏
页码:2360 / 2366
页数:7
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