Synthesis and dehydration of exo-2-(3-R-5-isoxazolyl)-5,6,6-trimethylbicyclo[2.2.1]heptan-endo-2-ols

The reaction of nitrile oxides with 2-exo-ethynyl-5,6,6-trimethylbicyclo[2.2.1]heptan-2-endo-ol resulted in 2-exo-(3-R-5-isoxazolyl)-5,6,6-trimethylbicyclo[2.2.1]heptan-2-endo-ols that on treatment with methanesulfonyl chloride in pyridine underwent dehydration to afford a mixture of 2-exo-(3-R-5-isoxazolyl)-5,5,6-trimethylbicyclo[2.2.1]hept-2-ene and 2-(3-R-5-Isoxazolyl)-4,7,7-trimethylbicyclo[2.2.1]hept-2-ene in 3; 1 ratio.