With this newly constructed rigid polycyclic system in place, the correct oxidation state and stereochemistry on C-14 and C-15 were installed. Site-specific reduction of C-14 was accomplished using L-selectride, followed by treating the crude material with NaBH4 to afford diol 32 (see the SI), which possessed the desired stereochemistry on C-15. Subsequently, C-14 was selectively returned to the ketone oxidation state with TEMPO/NaOCl. Other oxidants tested for this step showed poor selectivity (Table ). Remarkably, upon heating crude 17 with zinc powder in acetic acid, the Troc group was dismantled and the polycyclic ring system spontaneously unraveled through ring-chain tautomerization (presumably via 18) to liberate the deoxyportimine triflate 19 in 74% yield on gram-scale.