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Synthesis of musafluorone: a naphthoxanthenone isolated from Musa acuminata |
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| Authors: | Luisa Duque Jairo Sáez Bernd Schneider Felipe Otálvaro |
| Institution: | a Instituto de Química-Universidad de Antioquia, Calle 67# 53-108, A.A. 1226, Medellín, Colombia b Universidad Nacional de Colombia sede Medellín, Autopista Norte, Calle 64 Cra 65, A.A. 1027, Medellín, Colombia c Max-Planck Institut für Chemische Ökologie, Beutenberg Campus, Hans-Knöll-Strasse 8, 07745 Jena, Germany |
| Abstract: | 5-Methoxy-3H-naphtho2,1,8-mna]xanthen-3-one (musafluorone, 1), the only naphthoxanthenone reported so far from Musaceae, was synthesized starting from 2-naphthol in nine steps and resulted in an overall yield of 3%. Grignard addition of phenylmagnesium bromide to 4-methoxyperinaphthenone afforded the corresponding 4-methoxy-9-phenylphenalenone which, after epoxidation and methyl transposition, was subjected to a photochemical cyclization procedure to furnish 1. |
| Keywords: | Grignard addition Naphthoxanthenones Phenylphenalenones Photochemical cyclization |
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