130447-88-0

Upstream product

• 2305-13-7 3-Guaiacylpropanol 
• 106-95-6 allyl bromide 
• 97-53-0 4-allylguaiacol 

Downstream Products

• 854665-55-7 4-(3-Hydroxy-propyl)-2-methoxy-6-((E)-propenyl)-phenol 
• 919764-03-7 allyl 2-methoxy-4-(3-pivaloyloxypropyl)phenyl ether 
• 875213-64-2 2,2-Dimethyl-propionic acid 3-[4-hydroxy-3-methoxy-5-((E)-propenyl)-phenyl]-propyl ester 
• 875213-61-9 2,2-Dimethyl-propionic acid 3-[4-(allyl-dimethyl-silanyloxy)-3-methoxy-5-((E)-propenyl)-phenyl]-propyl ester 
• 875213-62-0 2,2-dimethyl-propionic acid 3-{2-[4-(2,2-dimethyl-propionyloxy)-3-methoxy-phenyl]-7-methoxy-3-vinyl-2,3-dihydro-benzofuran-5-yl}-propyl ester 
• 920518-59-8 2,2-dimethyl-propionic acid 3-{2-[4-(2,2-dimethyl-propionyloxy)-3-methoxy-phenyl]-3-formyl-7-methoxy-2,3-dihydro-benzofuran-5-yl}-propyl ester 
• 920518-80-5 2,2-dimethyl-propionic acid 2-(2,2-dimethyl-propionyloxy)-5-{5-[3-(2,2-dimethyl-propionyloxy)-propyl]-3-formyl-7-methoxy-2,3-dihydro-benzofuran-2-yl}-phenyl ester 
• 875213-63-1 2,2-dimethyl-propionic acid 2-(2,2-dimethyl-propionyloxy)-5-{5-[3-(2,2-dimethyl-propionyloxy)-propyl]-7-methoxy-3-vinyl-2,3-dihydro-benzofuran-2-yl}-phenyl ester 
• 125874-72-8 3-[2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]propan-1-ol 
• 6245-54-1 2-hydroxy-5-(3-hydroxy-propyl)-3-methoxy-benzaldehyde 
• 854664-22-5 2-allyl-4-(3-hydroxypropyl)-6-methoxyphenol 
• 919764-09-3 [2-methoxy-6-(methoxycarbonylmethyl)-4-(3-pivaloyloxypropyl)phenyl][3,4-di(pivaloyloxy)benzyl] ether 

Relevant academic research and scientific papers

A diastereoselective route to trans-2-aryl-2,3-dihydrobenzofurans through sequential cross-metathesis/isomerization/allylboration reactions: Synthesis of bioactive neolignans

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

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.