Diels-Alder reactions of cycloalkenones. 15. Synthesis of cis- and trans-.DELTA.6-4a-methyl-1-octalones
β Scribed by Angell, E. Charles; Fringuelli, Francesco; Pizzo, Ferdinando; Minuti, Lucio; Taticchi, Aldo; Wenkert, Ernest
- Book ID
- 126985191
- Publisher
- American Chemical Society
- Year
- 1989
- Tongue
- English
- Weight
- 292 KB
- Volume
- 54
- Category
- Article
- ISSN
- 0022-3263
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π SIMILAR VOLUMES
Stereocontrolled asymmetric synthesis and transannular Diels-Alder (TADA) reaction of a 14-membered transcis-cis (TCC) macrocyclic trienone with an activated dienophile leading to an A.B.C [6.6.6] tricycle having one angular methyl group is reported. The results of thermal and Lewis acid catalyzed T
Upon heating at 300%. TCC trienone 14 gave tricyclic ketone 15.
Upon heating at 3OO"C, C77 macrocyclic trienone 17 underwent 1,5-H shift and/or transannular DiebAlder yielding three tricyciic isomers 18, 19, and 20.