A powerful, novel approach to meroterpenes conicol, epiconicol and didehydroconicol has been achieved via a key step Diels-Alder reaction of (E)-3-methyl-1-(2',5'-dimethoxyphenyl)buta-1,3-diene as diene with methyl vinyl ketone, methyl acrylate or methyl propiolate as dienophiles. Activation by high pressure (9 kbar) or by the use of Lewis acid catalysts, allows the Diels-Alder reaction to proceed in excellent yield and diastereoselectively to form cyclohexenyl-benzene cycloadducts, which are useful precursors for conicols. The successful total syntheses of conicol, epiconicol and didehydroconicol, are described

A unified strategy for the synthesis of three conicol marine natural products

DI GIOIA, Maria Luisa;LEGGIO, Antonella;SICILIANO, Carlo;
2015

Abstract

A powerful, novel approach to meroterpenes conicol, epiconicol and didehydroconicol has been achieved via a key step Diels-Alder reaction of (E)-3-methyl-1-(2',5'-dimethoxyphenyl)buta-1,3-diene as diene with methyl vinyl ketone, methyl acrylate or methyl propiolate as dienophiles. Activation by high pressure (9 kbar) or by the use of Lewis acid catalysts, allows the Diels-Alder reaction to proceed in excellent yield and diastereoselectively to form cyclohexenyl-benzene cycloadducts, which are useful precursors for conicols. The successful total syntheses of conicol, epiconicol and didehydroconicol, are described
1-Aryl-1,3-butadienes; DielseAlder cycloaddition; Conicols
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/20.500.11770/151557
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