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- Title
Heterocyclic Analogs of Prostaglandins: I. Synthesis of 3-Alkyl(Aralkyl)-2,5-dihydrofuran-2-ones as Synthons for 11-Deoxy-10-oxaprostanoids.
- Authors
Pashkovskii, F. S.; Katok, Ya. M.; Khlebnikova, T. S.; Koroleva, E. V.; Lakhvich, F. A.
- Abstract
3-Acyl(arylmethyleneacyl)tetronic acids were synthesized. Selective hydrogenation of the carbonyl group in the acyl fragment and reduction of the conjugated double bond afforded in high yield the corresponding 3-alkyl(aralkyl) derivatives possessing either natural or modified prostaglandin α-chain. Reduction of the conjugated double bond in vinylogous 3-alkyl(aralkyl)tetronic acid amides with sodium cyanotrihydridoborate gave a mixture of stereoisomeric β-amino lactones which underwent retro-Michael elimination of the amine residue, leading to 3-alkyl(aralkyl)-2,5-dihydrofuran-2-ones. The latter can be regarded as synthons for 11-deoxy-10-oxaprostanoids.
- Subjects
ORGANIC compounds; PROSTANOIDS; INFLAMMATORY mediators; EICOSANOIC acid derivatives; ORGANIC chemistry; CARBON compounds
- Publication
Russian Journal of Organic Chemistry, 2003, Vol 39, Issue 7, p998
- ISSN
1070-4280
- Publication type
Article
- DOI
10.1023/B:RUJO.0000003193.75790.de