96909-18-1

Upstream product

• 108-24-7 acetic anhydride 
• 96909-09-0 1-Acetoxy-1-(3-methoxy-4,5-methylenedioxyphenyl)propanone 
• 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 
• 5780-07-4 3-methoxy-4,5-methylenedioxybenzaldehyde 
• 96909-07-8 3-(7-Methoxy-benzo[1,3]dioxol-5-yl)-2-methyl-oxirane-2-carboxylic acid methyl ester 
• 96909-11-4 2-Methoxycarbonyl-4-(3-methoxy-4,5-methylenedioxyphenyl)-3-methyl-2-buten-4-olide 
• 96909-15-8 (2RS,3SR,3aSR)-3,3a,4,5-Tetrahydro-2-(3-methoxy-4,5-methylenedioxyphenyl)-3-methyl-3a-(2-propenyl)-6(2H)-benzofuranone 
• 97091-08-2 (2SR,3SR,4RS)-4-(3-Methoxy-4,5-methylenedioxyphenyl)-3-methyl-2-(3-oxobutyl)-2-(2-propenyl)-4-butanolide 
• 96935-02-3 (4S,5R)-5-(7-Methoxy-benzo[1,3]dioxol-5-yl)-4-methyl-2-oxo-3-(3-oxo-butyl)-tetrahydro-furan-3-carboxylic acid methyl ester 
• 96913-18-7 (2SR,3SR,4RS)-2-(3,3-Ethylenedioxybutyl)-4-(3-methoxy-4,5-methylenedioxyphenyl)-3-methyl-2-(2-propenyl)-4-butanolide 
• 96909-08-9 Sodium; 3-(7-methoxy-benzo[1,3]dioxol-5-yl)-2-methyl-oxirane-2-carboxylate 

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.