Synthesis and Diels–Alder reactions of (E)-6,6-dimethoxy-3-hexen-2-one

Publisher Website
Google Scholar
Abstract
Treatment of 3,3-dimethoxypropanal (2) with (acetylmethylene)triphenylphosphorane (4) gives (E)-6,6-dimethoxy-3-hexen-2-one (5). Reaction of 5 with cyclopentadiene, 1,3-cyclohexadiene, anthracene, and 1,3-diphenylisobenzofuran gives Diels–Alder adducts, which on hydrolysis are converted to the corresponding keto aldehydes. Attempts to effect intramolecular aldol condensation of the latter were unsuccessful. Hydrolysis of the exo-acetyl adduct from 1,3-diphenylisobenzofuran with aqueous formic acid gives 4-acetyl-2,3,3a,4,5,9b-hexahydro-5,9b-diphenylnaphtho[1,2-b]furan-2,5-diol, via aldehyde formation and hydrolytic cleavage of the ether bridge. The adducts from cyclopentadiene under anhydrous acid conditions give 3-acetyl-9-methoxy-tetracyclo[4.3.0.02,4.03,7]nonane(27).

This publication has 0 references indexed in Scilit: