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Efficient Synthesis of Tyrosine-Derived Marine Sponge Metabolites via Acylation of Amines with a Coumarin

Harburn, J.J; Rath, N.P; Spilling, C.D

Authors

J.J Harburn

N.P Rath

C.D Spilling



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.

Citation

Harburn, J., Rath, N., & Spilling, C. (2005). Efficient Synthesis of Tyrosine-Derived Marine Sponge Metabolites via Acylation of Amines with a Coumarin. Journal of Organic Chemistry, 70(16), 6398-6403. https://doi.org/10.1021/jo050846r

Journal Article Type Article
Publication Date Jul 1, 2005
Deposit Date Oct 26, 2012
Journal Journal of Organic Chemistry
Print ISSN 0022-3263
Electronic ISSN 1520-6904
Publisher American Chemical Society
Peer Reviewed Peer Reviewed
Volume 70
Issue 16
Pages 6398-6403
DOI https://doi.org/10.1021/jo050846r