The Total Synthesis of (±)-Megaphyllone Acetate, A Cytotoxic Neolignan
- 1 January 1985
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 58 (1) , 346-351
- https://doi.org/10.1246/bcsj.58.346
Abstract
Conversion of 3-methoxy-4,5-methylenedioxybenzaldehyde into (2RS,3SR,4RS)-2-methoxycarbonyl-4-(3-methoxy-4,5-methylenedioxyphenyl)-3-methyl-4-butanolide (11) was carried out in seven steps via 1-acetoxy-1-(3-methoxy-4,5-methylenedioxyphenyl)propanone. The butanolide 11 was further converted into (2RS,3SR,3aRS,5RS)-3,3a,4,5-tetrahydro-5-methoxy-2-(3-methoxy-4,5-methylenedioxyphenyl)-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.Keywords
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