Acid-Catalyzed Diels-Alder Reactions of Cycloalkenones
- 1 January 1979
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 9 (5) , 391-394
- https://doi.org/10.1080/00397917908064167
Abstract
Whereas the Diels-Alder reaction has been in vogue as a facile method of six-membered ring construction for many years, its application to a one-step cis-octalone synthesis was precluded by discouraging, early reports on the conditions required for the interaction of dienes with 2-cyclohexenones and on the yields of the resultant adducts.1,2 It is quite conceivable that these observations were responsible in part for the minimization of use of an otherwise attractive route toward angularly alkylated six-membered polycycles in the field of steroid total synthesis. The discovery of Lewis acid catalysis of the cycloaddition of α, β-unsaturated carbonyl compounds3 has rekindled interest in the above reactions.4 The following discussion illustrates octaloneKeywords
This publication has 3 references indexed in Scilit:
- Synthesis of the Himachalenes by an Intramolecular Diels-Alder Reaction RouteSynthetic Communications, 1973
- ACCELERATION OF THE DIELS-ALDER REACTION BY ALUMINUM CHLORIDEJournal of the American Chemical Society, 1960
- Some Reactions of Δ2-Cyclohexenone, Including the Synthesis of Bicyclo(2,2,2)-octanedione-2,6Journal of the American Chemical Society, 1940