Completion of the Synthesis of Xylogranatopyridine B. With a scalable route to the tetracyclic carbon framework of xylogranatopyridine B (1-1) established, we explored the siteselective benzylic oxidation of the more electron-rich metaposition (C1) over the more electron-deficient ortho-position (C11) (Scheme 9). An extensive examination of oxidants identified a Cr(V)-complex, recently used by Baran for allylic oxidation, 44 as the optimal reagent for oxidation of the C1-benzylic position. The use of 10 equivalents of Cr(V) provided benzylic ketone 9-1 in 56 % yield with 27% recovered 3-1.