| Summary: | 碩士 === 輔仁大學 === 化學系 === 101 === This thesis started with the C-5 substituted 2-piperidinone 44.
Hydrolysis yielded the alcohol 45 with retention of configuration.
Compound 45 was then protected as the –OTBS group, and the tosyl group was cleaved by free radicals to give product 51. Treatment of compound 51 with Raney-Ni both cleaved the phenylthio group and
reduced the C＝C double bond to afford compound 18, which was reported in the literature as an intermediate for the synthesis of awajanomycin. The tosyl group of compound 45 was also cleaved, and
then the hydroxyl group was converted to the mesylate 53, which was further substituted by nucleophiles to yield compounds 54 and 58. Compound 54 was converted by click chemistry to yield triazoles 55 and 56, or hydrogenated and protected as the acetamide 57.
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