The optimal starting unit for the oxime fragment was α-ionone (11-1), a widely available terpene building block, as it possesses many of the necessary structural features and oxidation states which are present in the oxime coupling fragment (10-2). One challenge with employing α-ionone (11-1) is that it is available as the racemate, and thus would need to be resolved prior to the fragment union. Although there are copious stepwise routes to access enantioenriched α-ionone (11-1), we regarded a direct kinetic resolution as optimal for an expedited synthesis of 11-2. The viability of this approach was guaranteed by a previously reported synthesis of (⎯)-epoxy-αionone (11-2) via lipase-resolution, albeit over a five-step sequence (Scheme 11B). The attempted synthesis of the oxime fragment commenced with kinetic resolution of α-ionone (11-1) using Jacobsen's commercially available (S,S)-Mn-Salen epoxidation catalyst, 4-PPNO, and buffered bleach as the terminal oxidant to provide (⎯)-11-2 in 43% yield, 89:11 er, and 10:1 dr on 100 gram scale (Scheme 11B). Examination of alternative metal Salen catalysts or oxidants resulted in diminished yield and er. Additionally, Shi epoxidation conditions failed to convert 11-1 to 11-2. A hydrosilylation of the enone functionality in 11-2 with [Rh(COD)(OH)]2 and phenyldimethylsilane afforded enoxysilane 11-3 in 89% yield on decagram scale. Replacement of phenyldimethylsilane with triethylsilane resulted in diminished yield, while utilizing [RhH(PPh3)4] as the catalyst completely suppressed the desired reactivity (Scheme 11, Table ). Other transition metal-catalyzed or -mediated hydrosilylation conditions, such as those invovling Stryker's reagent, Karstedt's catalyst, or Pd-catalyzed conditions, 77 afforded the desired product (11-3) in decreased yields. Subjection of enoxysilane 11-3 to ozonolytic oxidative cleavage conditions followed by addition of Jones reagent resulted in 11-5 in 51% yield. The product 11-5 may arise from cyclization of the carboxylic acid onto a tertiary carbocation (11-4). This pathway is suggested as retention of stereochemistry is observed, which is presumably due to geometric constraints that preclude an SN2-type epoxide opening. Treatment of 11-5 with Böhme's salt 21 gave rise to an intermediate ammonium salt (11-6), and after β-elimination an unstable exocyclic enone intermediate 11-7 was observed. Enone 11-7 was characterized as a crude mixture of compounds and was found to decompose rapidly while neat, or in CDCl3 with a half-life of approximately two hours at room temperature.