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Synthesis of 4-methoxy-1H-phenalen-1-one: a subunit related to natural phenalenone-type compounds |
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| Authors: | Juliana Nanclares, Jesú s Gil, Benjam&#x n Rojano, Jairo Saez, Bernd Schneider,Felipe Ot lvaro |
| Affiliation: | aInstituto de Quı´mica-Universidad de Antioquia, Calle 67# 53-108, A.A. 1226 Medellı´n, Colombia bUniversidad Nacional de Colombia sede Medellı´n, Autopista Norte, Calle 64 Cra 65, A.A. 1027 Medellı´n, Colombia cMax-Planck Institut für Chemische Ökologie, Beutenberg Campus, Hans-Knöll-Strasse 8, 07745 Jena, Germany |
| Abstract: | 4-Methoxy-1H-phenalen-1-one (4-methoxyperinaphthenone, 1), a subunit found in some Musa phytoalexins and related natural products from the Haemodoraceae, was synthesized starting from 2-methoxynaphthalene in five steps and an overall yield of 36%. A Heck–Fujiwara coupling between ethyl acrylate and 1-bromonaphthalene afforded the corresponding (E)-naphthylpropanoic acid which, after hydrogenolysis, was subjected to a one-pot Friedel–Crafts acylation–DDQ dehydrogenation procedure to furnish 1. |
| Keywords: | Friedel–Crafts acylation Heck coupling Phenalenones |
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