☆ 4.7 Article

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

JOURNAL OF ORGANIC CHEMISTRY (2011)

Journal

JOURNAL OF ORGANIC CHEMISTRY

Volume 76, Issue 7, Pages 2360-2366

Publisher

AMER CHEMICAL SOC

DOI: 10.1021/jo2000868

Keywords

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Categories

Chemistry, Organic

Funding

EPSRC
AstraZeneca
University of Sheffield, U.K.

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Abstract

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.

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