The addition of organolithium reagents to the oxa tricyclic ketone 1 occurs stereospecifically to produce the corresponding tertiary carbinols 2a-d. When the alcohols 2a-d are treated with Tic&, ring fragmentation and dehydration occur to produce good yields of 5, 6- dihydrobenzaldehydes 3a-d. Oxidation of aldehydes 3a-d then leads to the corresponding meta-substituted benzaldehydes 4a-d. Alternatively, use of the Lewis acid Me, BBr did not ...
![6-phenyl-2-oxatricyclo[2.2.2.03,5]octan-6-ol Structure](https://image.chemsrc.com/caspic/085/103668-94-6.png)
