However, after attempting benzylic oxidation conditions, similar to the conditions described in Scheme 9, conversion to 13-2 was not observed. Puzzled by this result, the calculated energies of the radicals and carbocations at positions A and B for C3-deoxy-xylogranatin F (10-1) and the corresponding tetracyclic intermediate (3-1) in the xylogranatopyridine B route were examined (Scheme 13C). Interestingly, DFT calculations at three different levels of theory showed that while carbocation A energy for the tetracyclic intermediate (3-1) en route to xylogranatopyridine B is 3.5-5.5 kcal/mol more stable than the corresponding carbocation B, the carbocation A and B have comparable energies for the more electron deficient C3deoxy-xylogranatin F (10-1). In addition, while radical A and B for 3-1 have similar energies, radical B for 10-1 is 2.6-2.8 kcal/mol more stable than radical A. These calculations indicated that the selectivity would likely favor the position B in the case of 10-1, especially considering steric effects. That said, initial attempts did not lead to either oxidation product for the more deactivated substrate. Therefore, we developed alternative plans with early introduction of the C3 oxidation state.