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

  title={Simple Synthesis of 5-Substituted Resorcinols: A Revisited Family of Interesting Bioactive Molecules.},
  author={Emma Alonso and Diego J. Ram{\'o}n and Miguel Yus},
  journal={The Journal of organic chemistry},
  volume={62 2},
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… Expand
Stereoselective Synthesis of (E)‐Hydroxystilbenoids by Ruthenium‐Catalyzed Cross‐Metathesis
An efficient and highly stereoselective synthetic procedure is reported for the construction of symmetrical and unsymmetrical (E)-polymethoxystilbene and (E)-polyhydroxystilbene derivatives. TheExpand
On the deprotonation of η6-1,3-dimethoxybenzene-Cr(CO)3 derivatives: Influence of the reaction conditions on the regioselectivity
Abstract The regioselectivity of deprotonation/alkylation reactions of η6-1,3-dimethoxybenzene-Cr(CO)3 (5), η6-1,3-dimethoxy-5-methylbenzene-Cr(CO)3 (6) and 2-substituted derivatives of theseExpand
Practical generation of 3,5-dimethoxybenzyllithium: application to the synthesis of 5-substituted-resorcinols
Reductive lithiation of 3,5-dimethoxybenzyl methyl ether was successfully performed with lithium wire and a catalytic amount of naphthalene in dry tetrahydrofuran at −15°C, leading to theExpand
Lithiophenylalkyllithiums: new dilithium reagents having both sp2- and sp3-hybridised remote carbanionic centres
Abstract The reaction of chloro-(2-chloroethyl)benzenes (1), 4-chloro-(3-chloropropyl)benzene (3) or 4-chlorophenyl chloromethyl ether (5) with lithium power using naphthalene as the electron shuttleExpand
Abstract The reaction of N , N -disubstituted benzamide derivatives 1 with lithium and a catalytic amount of naphthalene (4 mol %) in the presence of carbonyl compounds (Barbier-type conditions) ledExpand
Synthesis of Piceatannol, an Oxygenated Analog of Resveratrol.
Piceatannol (3,3',4,5'-tetrahydroxy-trans-stilbene, 2), an oxygenated analog of resveratrol, was synthesized, and possesses many kinds of beneficial effects such as anticancer activity. Expand
Synthesis of methylated resveratrol and analogues by Heck reactions in organic and aqueous solvents
The Heck reaction under phosphane free conditions using oxime-derived palladacycles or Pd(OAc)2 as catalysts is a general methodology for the synthesis of methoxylated (E)-stilbene derivatives.Expand
Synthesis of 5‐Substituted Resorcinol Derivatives via Cross‐Coupling Reactions
Suzuki and Stille cross-coupling reactions were utilized in the synthesis of 5-substituted 1,3-dimethoxybenzene and 5-substituted resorcinol derivatives. The substituted resorcinol derivatives wereExpand
Preparation of α,n-dilithiotoluene equivalents. Synthesis of tamoxifen
Abstract The successive reaction of chlorobenzyl alcohols with n -butyllithium and lithium powder in the presence of a substoichiometric amount of 4,4′-di- tert -butylbiphenyl (DTBB) at −78°C yieldsExpand
4-(6-Hydroxy-2-naphthyl)-1,3-bezendiol: a potent, new tyrosinase inhibitor.
4-(6-hydroxy-2-naphthyl)-1,3-bezendiol (HNB), a new family of hydroxyl substituted phenyl naphthalenes, is synthesized as the isosteres of oxyresveratrol to suggest that HNB can suppress the production of melanin via the modulation of tyrosinase activity. Expand