20736-21-4Relevant articles and documents
NOVEL 1-PHENYLMONO- OR -POLYHYDROXYPROPANE COMPOUNDS, COMPOSITIONS AND COSMETIC USES THEREOF
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Paragraph 26; 27, (2017/04/04)
The present invention relates to novel compounds of formula (I) to compositions comprising same, and also to the use thereof for preventing and/or cosmetically treating the signs of aging of the skin.
A diastereoselective route to trans-2-aryl-2,3-dihydrobenzofurans through sequential cross-metathesis/isomerization/allylboration reactions: Synthesis of bioactive neolignans
Hemelaere, Rémy,Carreaux, Fran?ois,Carboni, Bertrand
supporting information, p. 2470 - 2481 (2015/04/22)
A new highly diastereoselective synthetic route to trans-2,3-dihydrobenzofuran systems, in particular those bearing an aryl substituent at the C2 position, is described. The cornerstone of our strategy is the implementation of a cross-metathesis/isomerization/allylboration sequence starting from 2-allyl-substituted phenols and aldehydes. After an intramolecular Mitsunobu cyclization step, the anti-homoallylic alcohols allow the synthesis of the desired skeleton in a stereoselective fashion. As an illustration, we used this strategy for the preparation of the dihydrodehydrodiconiferyl alcohol (1a), a natural dihydrobenzofuran neolignan, as well as for a formal synthesis of its O-demethylated derivative 1b. An enantioselective version of this approach employing a chiral phosphoric acid in the allylboration step is also studied.
Benzo[f][1,2]oxasilepines in the synthesis of dihydro[b]benzofuran neolignans
García-Mu?oz, Sergio,Jiménez-González, Leticia,álvarez-Corral, Míriam,Mu?oz-Dorado, Manuel,Rodríguez-García, Ignacio
, p. 3011 - 3013 (2007/10/03)
A short synthesis of neolignans with a dihydrobenzo[b]furan skeleton is described. The strategy is based on a ring-closing metathesis to produce benzo[f][1,2]oxasilepines which are condensed with aromatic aldehydes in a modified Sakurai-Hosomi reaction. Natural dihydrodehydrodiconiferyl alcohol (1) and 3-O-demethyldihydrodehydrodiconiferyl alcohol (2) have been prepared in this way. Georg Thieme Verlag Stuttgart.
Synthesis of Coniferyl and Dihydroconiferyl Derivatives Using Radical Bromination with N-Bromosuccinimide as the Key Step
Lindeberg, Otto
, p. 15 - 20 (2007/10/02)
Coniferyl and dihydroconiferyl derivatives have been synthesized by reacting bromides, obtained from allylic and benzylic brominations using N-bromosuccinimide (NBS), with appropriate nucleophiles.For instance, NBS bromination of eugenol acetate, followed by replacement of bromine by an acetoxy group and subsequent reduction with lithium aluminium hydride, afforded coniferyl alcohol in 65percent overall yield.Due to the availability of the starting materials (eugenol and isoeugenol) and the good overall yields obtained, these synthetic routes compete well with other methods of preparation.