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Updated: Jun 3, 2026

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Synthesis of the core ring system of the yuzurimine-type Daphniphyllum alkaloids by cascade condensation,
Iain Coldham1, Luke Watson, Harry Adams
1Department of Chemistry, University of Sheffield, Brook Hill, Sheffield S3 7HF, UK. i.coldham@sheffield.ac.uk
Abstract:
Addition of hydroxylamine to substituted 4-chlorobutanals 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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