Functionalization of (R)-3-(3-Acetoxypropyl)-2,3-dihydro-7-isopropyl-3,4-dimethylnaphthofuran-2-one and Some Related Compounds

Article abstract of DOI:10.1246/bcsj.56.2985

Oxidation of (R)-3-(3-acetoxypropyl)-2,3-dihydro-6-hydroxy-7-isopropyl-3,4-dimethylnaphtho<2,3-b>furan-2-one with Fremy's radical afforded the corresponding o-quinone, which was converted into (R)-5,6,8-triacetoxy-3-(3-acetoxypropyl)-2,3-dihydro-7-isopropyl-3,4-dimethylnaphtho<2,3-b>furan-2-one and its 5,6,9-triacetoxy isomer. (R)-3-(3-Acetoxypropyl)-2,3-dihydro-7-isopropyl-3,4-dimethylnaphtho<2,3-b>furan-2-one was also converted into (R)-9-acetoxy- and (R)-5,8,9-triacetoxy-2,3-dihydro-7-isopropyl-3-(3-methoxypropyl)-3,4-dimethylnaphtho<2,3-b>furan-2-one.Transformation of (R)-2,3-dihydro-6-hydroxy-3-(3-hydroxypropyl)-7-isopropyl-3,4-dimethylnaphtho<2,3-b>furan-2-one into (R)-6-acetoxy-3-allyl-2,3-dihydro-7-isopropyl-3,4-dimethylnaphtho<2,3-b>furan-2-one was also achieved.