Improved synthesis of 4-phenylphenalenones: the case of isoanigorufone and structural analogs

…, W Hidalgo, J Sáez, J Gil, B Schneider, F Otálvaro

Index: Cano, Marisol; Rojas, Carlos; Hidalgo, William; Saez, Jairo; Gil, Jesus; Schneider, Bernd; Otalvaro, Felipe Tetrahedron Letters, 2013 , vol. 54, # 4 p. 351 - 354

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Citation Number: 4

Abstract

2-Hydroxy-4-phenyl-1H-phenalen-1-one (isoanigorufone, 1), a phytoalexin exclusive of Musaceae, was synthesized starting from 3-(2-hydroxynaphthalen-1-yl) propanenitrile in nine steps in an overall yield of 10%. Hydrolysis of ethyl 3-(2-phenylnaphthalen-1-yl) propanoate obtained from Suzuki–Miyaura coupling between the parent triflate and phenylboronic acid afforded the corresponding propionic acid which, after Friedel–Crafts ...