Over the past two decades the chemistry of 3-oxidopyrylium ylide has been receiving considerable interest from the synthetic organic chemists around the world. Oxidopyrylium is a reactive species, readily undergoes cycloaddition reaction with suitable dipolarophiles to generate oxa-bridge cycloheptanoid derivatives with proper stereo- and regiochemistry. The work presented here deals with our findings of one-pot reduction of enones of the [5+2] cycloadducts to the corresponding tetrahydro derivatives with nickel boride (generated in situ) using THF as solvent. It is worth to mention that reaction of the cycloadducts with Sodium borohydride and/or Lithium aluminum hydride always led a mixture of 1,2- and 1,4-reduction products. The yields of nickel boride reductions are generally more than 90%. The resultant tetrahydro-derivatives are transformed to the corresponding cycloheptenoids by removing the bridging ether.