185840-31-7

Upstream product

• 167466-94-6 (1S,2R,5S,7S,8R,4'S)-tert-butyl-2-benzyloxy-8-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-6-oxo-tricyclo<3.2.1.0^2,7>octane-1-carboxylate 

Downstream Products

• 196614-83-2 tert-butyl (1R,2S,3S,6R,7S,4'S)-6-benzyloxy-7-ethenyl-3-hydroxy-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-bicyclo[4.1.0]heptane-1-carboxylate 

Relevant academic research and scientific papers

Baeyer-Villiger oxidation of 6-oxotricyclo-[3.2.1.02,7]octanes; Regioselective opening of push-pull substituted cyclopropanes

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.

Highly functionalized enantiopure oxatricyclo[3.3.1.04,6]nonanes; Selective opening of an activated cyclopropane ring

Baeyer-Villiger oxidation of 3 gives solely the lactones 4. The double-pull-push substituted cyclopropane moiety of 4b is selectively opened upon hydrogenolysis of the benzyl ether to yield ketone 5.