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

页码：2360 / 2366

页数：7

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