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Updated: Apr 23, 2026

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
Published on: April 24, 2018
Synthesis of the putative structure of 15-oxopuupehenoic acid
Ettahir Boulifa1, Antonio Fernández, Esteban Alvarez
1Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada , 18071 Granada, Spain.
Abstract:
Synthesis of the putative structure of the marine natural 15-oxopuupehenoic acid has been achieved starting from commercial (-)-sclareol. Key steps of the synthetic sequence are the Robinson annulation of a β-ketoester and methyl vinyl ketone and an unprecedented cyclization of the resulting α,β-enone, which is mediated by tin(IV) chloride in the presence of N-phenylselenophthalimide. The physical properties of the synthetic compound are somewhat different from those reported for the natural product.
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