alexa Efficient synthesis of tyrosine-derived marine sponge metabolites via acylation of amines with a coumarin.
Chemical Engineering

Chemical Engineering

Journal of Thermodynamics & Catalysis

Author(s): Harburn JJ, Rath NP, Spilling CD

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Abstract Condensation of N-acetylglycine with aldehyde 15 in acetic anhydride gave acetamido coumarin 16. Hydrolysis to the enol coumarin 17 and reaction with hydroxylamine gave the oximino coumarin 18. Reaction of the oximino coumarin 18 with a range of nucleophiles gave the phenolic oximes in excellent yield. The rates of acylation of histamine with the oximino coumarin 18 and methyl ester 9 were compared. Oxidative spirocyclization of three representative phenolic oximes with polymer-supported (diacetoxyiodo) benzene gave the spiroisoxazolines. This article was published in J Org Chem and referenced in Journal of Thermodynamics & Catalysis

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