A concise total synthesis of biologically active frutinones via tributylphosphine-catalyzed tandem acyl transfer-cyclization |
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| Institution: | 1. Laboratorio de Cristalografía, Departamento de Química, Facultad de Ciencias, Universidad de Los Andes, Mérida 5101, Venezuela;2. Departamento de Química, Facultad de Ciencias Básicas, Universidad de Antofagasta, Campus Coloso, Antofagasta 1240000, Chile;3. Cátedras Conacyt - Instituto Mexicano del Petróleo, Centro de Tecnologías para Exploración y Producción, Boca del Rio, Mexico;4. Escuela Superior de Ingeniería Química e Industrias Extractivas, Instituto Politécnico Nacional, Ciudad de México, Mexico |
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| Abstract: | A concise and step-economical total synthesis of biologically active frutinones has been achieved. Tributylphosphine (PBu3) efficiently induced the tandem acyl transfer-cyclization of carbonates 5 to afford 3-methoxycarbonylflavone derivatives 4 in excellent yields. Finally, concomitant deprotection and lactonization under acidic conditions furnished the desired frutinones A (1a), B (1b), and the proposed structure of frutinone C (1c). |
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| Keywords: | Total synthesis Flavone Regioselective Tandem reaction Organocatalyst |
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