96909-07-8

Upstream product

• 17639-93-9 2-chloro-propionic acid methyl ester 
• 5780-07-4 3-methoxy-4,5-methylenedioxybenzaldehyde 
• 149-91-7 3,4,5-trihydroxybenzoic acid 
• 22934-58-3 methyl 7-methoxybenzo[d][1,3]dioxole-5-carboxylate 
• 3934-84-7 3,4-dihydroxy-5-methoxybenzoic acid 
• 3934-86-9 methyl 3,4-dihydroxy-5-methoxybenzoate 
• 22934-59-4 (7-methoxybenzo[d][1,3]dioxol-5-yl)methanol 

Downstream Products

• 96909-18-1 (+/-)-Demethoxymegaphyllone acetate 

Relevant academic research and scientific papers

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

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.