Regioselective reduction and ring cleavage of polycyclic barbituric acid analogues derived from intramolecular hetero-Diels-Alder reactions

Authors
Tietze, LF Ott, C Geissler, H Haunert, F
Citation
Lf. Tietze et al., Regioselective reduction and ring cleavage of polycyclic barbituric acid analogues derived from intramolecular hetero-Diels-Alder reactions, EUR J ORG C, (9), 2001, pp. 1625-1630
Citations number
18
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
9
Year of publication
2001
Pages
1625 - 1630
Database
ISI
SICI code
1434-193X(200105):9<1625:RRARCO>2.0.ZU;2-F
Abstract
The annulated and bridged dihydropyrans 6-8 obtained by a domino-Knoevenage l-hetero-Diels-Alder reaction with N,N ' -dimethylbarbituric acid were redu ced with excess DI-BAL-H at -78 degreesC to give the corresponding 3-desoxy derivatives, which were then hydrolyzed to the lactones 14-16 with HCl. Co mpounds 15 and 16 were further reduced to the cor responding lactols. Elimi nation finally yielded the new functionalized heterocycles 18 and 20.