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Alonso E, Ramón DJ, Yus M. Simple Synthesis of 5-Substituted Resorcinols: A Revisited Family of Interesting Bioactive Molecules. J Org Chem. 1997;62(2):417-421doi: 10.1021/jo9610624.
Alonso, E., Ramón, D. J., & Yus, M. (1997). Simple Synthesis of 5-Substituted Resorcinols: A Revisited Family of Interesting Bioactive Molecules. The Journal of organic chemistry, 62(2), 417-421. https://doi.org/10.1021/jo9610624
Alonso, Emma, et al. "Simple Synthesis of 5-Substituted Resorcinols: A Revisited Family of Interesting Bioactive Molecules." The Journal of organic chemistry vol. 62,2 (1997): 417-421. doi: https://doi.org/10.1021/jo9610624
Alonso E, Ramón DJ, Yus M. Simple Synthesis of 5-Substituted Resorcinols: A Revisited Family of Interesting Bioactive Molecules. J Org Chem. 1997 Jan 24;62(2):417-421. doi: 10.1021/jo9610624. PMID: 11671418.
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J Org Chem. 1997 Jan 24;62(2):417-421. doi: 10.1021/jo9610624.

Simple Synthesis of 5-Substituted Resorcinols: A Revisited Family of Interesting Bioactive Molecules.

The Journal of organic chemistry

Emma Alonso, Diego J. Ramón, Miguel Yus

Affiliations

  1. Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Alicante, Apdo. 99, E-03080-Alicante, Spain.

PMID: 11671418 DOI: 10.1021/jo9610624

Abstract

The reaction of 3,5-dimethoxybenzyl trimethylsilyl ether (3) with different aldehydes (n-PrCHO, n-C(11)H(23)CHO, MeCHO, PhCHO) in the presence of lithium powder and a catalytic amount of naphthalene (4 mol %) gave, after hydrolysis, the expected alcohols 4 in moderate yields. The dehydroxylation of these compounds through the corresponding mesylates 5 or directly from benzylic derivatives by catalytic hydrogenation, afforded compounds 6, which are finally demethylated to yield 5-alkyl-3,5-dihydroxyresorcinols, such as olivetol (7a), grevillol (7b), 1,3-dihydroxy-5-propylbenzene (7c), or dihydropinosilvine (7d). Dehydration of alcohol derivatives 4 followed by demethylation led to hydroxylated stilbene-type structures, such as pinosilvine (9d), resveratrol (9e), or piceatannol (9f), which in some cases can be hydrogenated to give saturated molecules such as combretastanin B-4 tetramethyl ether (6f) or chrysotobibenzyl (6g). Finally, when the naphthalene-catalyzed lithiation of compound 3 was performed in the presence of other electrophiles [Me(3)SiCl, t-BuCHO, CH(3)(CH(2))(4)CHO, 4-Me(3)SiOC(6)H(4)CHO, (CH(2))(5)CO, PhN=C=O, PhN=CHPh], the expected reaction products 12 were isolated, after hydrolysis.

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