A New Method for the Synthesis of 3,5-Disubstituted 2(5H)-Furanones. Synthesis of (±)-Acarenoic Acid
- 1 August 1987
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 60 (8) , 2917-2921
- https://doi.org/10.1246/bcsj.60.2917
Abstract
Heating of 3,5-disubstituted 4-bromo-3-methoxycarbonyldihydro-2(3H)-furanones with NaI in 3-pentanone gave 3,5-disubstituted 2(5H)-furanones in 55.8–93.3% isolated yields. A total synthesis of (±)-acarenoic acid was established in 33% overall yield via 4 steps.Keywords
This publication has 9 references indexed in Scilit:
- A Highly Stereoselective Synthesis of (E)-Enol Lactones by the Wittig Reaction of Cyclic Anhydrides with (α-Alkoxycarbonylethylidene)triphenylphosphoraneBulletin of the Chemical Society of Japan, 1987
- Highly stereo- and regioselective alkylation of alkylidenemalonates. Application to the synthesis of (.+-.)-canadensolideThe Journal of Organic Chemistry, 1986
- A New Synthesis of Pyrocin and Related CompoundsBulletin of the Chemical Society of Japan, 1977
- Recent advances in the chemistry of unsaturated lactonesChemical Reviews, 1976
- Chemistry of α-Haloaldehyde. VI. Reaction of 2-Chloro-2-methylpropanal with Benzoylacetonitrile in the Presence of Potassium CarbonateBulletin of the Chemical Society of Japan, 1974
- Chemistry of .alpha.-halo aldehydes. IV. Reaction of 2-halo-2-methylpropanal with acylacetates in the presence of baseThe Journal of Organic Chemistry, 1974
- Chemistry of .alpha.-haloaldehydes. III. Reaction of 2-halo-2-methylpropanal with malonic esters in the presence of potassium carbonate. (Synthesis of .gamma.-butyrolactones)The Journal of Organic Chemistry, 1973
- Chemical Studies on Lichens. 7. Acaranoic and Acarenoic Acid, Two New Aliphatic Lichen Acids.Acta Chemica Scandinavica, 1967
- Condensation Reactions. II. Alkylidene Cyanoacetic and Malonic EstersJournal of the American Chemical Society, 1941