22263-98-5Relevant academic research and scientific papers
Synthesis of isocoumarin compounds, 8-Hydroxy-6-Methoxy-3-Pentyl-1H-Isochromen-1-One and Fusariumin analog using palladium-Catalyzed carbonylation trapping with O-enolate
Asai, Masaki,Hattori, Yasunao,Makabe, Hidefumi
, p. 1542 - 1553 (2017)
Concise synthesis of 6,8-dialkoxyisocoumarin framework was achieved using Pd-catalyzed carbonylation trapping with O-enolate. This methodology was applied to the synthesis of 8-hydroxy-6-methoxy-3-pentyl-1H-isochromen-1-one isolated from Tessmannia densiflora and fusariumin analog.
Simple synthesis of 5-substituted resorcinols: A revisited family of interesting bioactive molecules
Alonso, Emma,Ramon, Diego J.,Yus, Miguel
, p. 417 - 421 (2007/10/03)
The reaction of 3,5-dimethoxybenzyl trimethylsilyl ether (3) with different aldehydes (n-PrCHO, n-C11H23CHO, 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 [Me3SiCl, t-BuCHO, CH3(CH2)4CHO, 4-Me3SiOC6H4CHO, (CH2)5CO, PhN = C = O, PhN = CHPh], the expected reaction products 12 were isolated, after hydrolysis.
