Synthesis p. 917 - 920 (1997)
Update date:2022-08-03
Topics:
Braun, Norbert A.
Stumpf, Natascha
Spitzner, Dietrich
Cascade reactions of cyclic dienolates 1 with enantiopure Michael accepters 2 lead to 3. Oxidation of 3 under Baeyer-Villiger conditions gave solely the lactones 4. The double-push-pull substituted cyclopropane moiety of 4a was selectively opened upon hydrogenolysis to yield oxabicyclo[3.3.1]nonane 6. Reduction of lactone 4a gave the hemiacetal 7. It was converted to the vinylcyclopropane 10 which was hydrogenated to give the highly functionalized cycleheptane 11 and oxabicyclo[3.2.1]octanes 12.
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