Inter- and Intramolecular Diels-Alder Cycloaddition of Enantiopure 4,5-O, C-Functionalized Cyclohex-2-Enone and Its Derivatives Prepared fromD-Glucose1
- 1 May 1997
- journal article
- research article
- Published by Taylor & Francis in Journal of Carbohydrate Chemistry
- Vol. 16 (4-5), 441-457
- https://doi.org/10.1080/07328309708007327
Abstract
The Lewis acid catalyzed reaction of a D-glucose derived functionalized cyclohex-2-enone 1 with furan provided the 1,4-conjugate adducts 3 and 4. On the other hand, thermal intermolecular Diels-Alder cycloaddition of 1 with 1,3-cyclohexadiene provided two endo-cycloadducts 5 and 6 in a good combined yield. The intramolecular cycloaddition of sorbic acid ester 20 of the allylic alcohol 19, prepared from 1, proceeded under thermal conditions to give a mixture of highly functionalized decalin derivatives 21-23, whose stereostructures were determined by chemical modification.Keywords
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