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

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Hidalgo,  William
Research Group Biosynthesis / NMR, MPI for Chemical Ecology, Max Planck Society;
IMPRS on Ecological Interactions, MPI for Chemical Ecology, Max Planck Society;

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Schneider,  Bernd
Research Group Biosynthesis / NMR, MPI for Chemical Ecology, Max Planck Society;

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Citation

Cano, M., Rojas, C., Hidalgo, W., Sáez, J., Gil, J., Schneider, B., et al. (2012). Improved synthesis of 4-phenylphenalenones: the case of isoanigorufone and structural analogs. Tetrahedron Letters, 54, 351-354. doi:10.1016/j.tetlet.2012.11.118.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0010-257F-3
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 acylation and bromine-mediated dehydrogenation, was subjected to Yang–Finnegan epoxidation to furnish 1. The preparation of analogs using this procedure is also discussed. Isoanigorufone was synthesized using a nine-step procedure including a Suzuki–Miyaura coupling and a Friedel–Crafts acylation. The synthesis of structural analogs was also explored.