Synthesis of the Putative Structure of 15-Oxopuupehenoic Acid
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Boulifa, Ettahir; Fernández, Antonio; Alvarez, Esteban; Alvarez-Manzaneda Roldán, Ramón Jesús![Autoridad Universidad de Almería Autoridad Universidad de Almería](/themes/Mirage2/images/autoridades/autoridad.png)
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2014-10-02Resumen
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.