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Intramolecular diels-alder reactions of 2-alkenyl-1,2-dihydropyridines. An approach to the synthesis of the cis-decahydroquinoline ring system.

✍ Scribed by Daniel L. Comins; Abdul H. Abdullah; Roy K. Smith

Publisher: Elsevier Science
Year: 1983
Tongue: French
Weight: 181 KB
Volume: 24
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)88002-8

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✦ Synopsis

In refluxing decalin P-alkenyl-1-alkoxycarbonyl-1,2_dihydropyridines undergo an intramolecular Diels-Alder reaction to provide novel polycyclic compounds. The cis-decahydroquinoline ring system can be prepared from the appropriate Diels-Alder product utilizing a ring-opening reverse Mannich reaction. In recent years there has been considerable interest in the synthetic uses of the intramolecular Diels-Alder reacti0n.l This reaction has been especially useful for the synthesis of polycyclic natural products as it provides for the regioselective and stereospecific introduction of multiple chiral centers. Certain 1,2_dihydropyridines are useful dienes for the intermolecular Diels-Alder cycloaddition,2y3 however, only a few examples of 1. For reviews see E. Ciganek, a Reactions, in press; G. Brieger and J.N. Bennett, Chem.Rev.,

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