The total synthesis of (±)-megaphyllone acetate, a cytotoxic neolignan

Article abstract of DOI:10.1246/bcsj.58.346

Conversion of 3-methoxy-4,5-methylenedioxybenzaldehyde into (2RS,3SR,4RS)-2-methoxycarbonyl-4-(3-methoxy-4,5-methylenedioxyphenyl)-3-m ethyl-4-butanolide was carried out in seven steps via 1-acetoxy-1-(3-methoxy-4,5-methylenedioxyphenyl)propanone. The butanolide was further converted into (2RS,3SR,3aRS,5RS)-3,3a,4,5-tetrahydro-5-methoxy-2-(3-methoxy-4,5-methylen edioxyphenyl)-3-methyl-3a-(2-propenyl)-6(2H)-benzofuranone (22) in eight steps. Reduction of 22 with lithium aluminium hydride followed by acetylation with acetic anhydride in pyridine afforded (±)-megaphyllone acetate.