A New Synthesis of 4-Methoxy-6-valeryl-5,6-dihydro-2-pyrone
- 1 August 1977
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 50 (8) , 2191-2192
- https://doi.org/10.1246/bcsj.50.2191
Abstract
The reaction of ethyl 2-acetoxy-3-oxoheptanoate with γ-bromo-β-methoxy-cis-crotonate in the presence of sodium ethoxide afforded diethyl 3-methoxy-5-hydroxy-5-valeryl-2-hexenedioate (7) in 65% yield. Treatment of 7 with a dilute aqueous NaOH in acetone gave (±)-4-methoxy-6-valeryl-5,6-dihydro-2-pyrone, a key intermediate leading to pestalotin, in 41% yield.Keywords
This publication has 5 references indexed in Scilit:
- Ergiebige Synthese von (±)‐Pestalotin und (±)‐Epipestalotin. Optisch reines (−)‐Pestalotin durch asymmetrische SyntheseAngewandte Chemie, 1974
- Isolation and Structure of Pestalotin, a Gibberellin Synergist fromPestalotia cryptomeriaecolaAgricultural and Biological Chemistry, 1972
- Structure of a new fungal lactone, LL-P880.alpha., from an unidentified Penicillium speciesThe Journal of Organic Chemistry, 1972
- Syntheses of Reductones. A New Method of Synthesizing 2-Acetoxy-1, 3-dicarbonyl CompoundsBulletin of the Chemical Society of Japan, 1967
- Studies in Chemotherapy. X. Antithyroid Compounds. Synthesis of 5- and 6- Substituted 2-Thiouracils from β-Oxoesters and Thiourea1Journal of the American Chemical Society, 1945