Boc-activation of amide 2a and treatment of intermediate 19 with lithium hydrogen peroxide 31 afforded cis-carboxylic acid 21 in 71% yield (over 2 steps). Reduction of the same intermediate 19 with LiAlH4 gave alcohol 20 in 62% yield. Alternatively, alcohol 20 could be accessed by reduction of 21 using BH3•SMe2. Acid 21 was converted to primary amide 22 by anhydride formation with isobutyl chloroformate, followed by treatment with aqueous NH4OH. Notably, conversion of 2a to the primary amide 22 using IBX or ozonolysis conditions was unsuccessful due to alternative oxidation of the electron-rich PMP substituent. A Pd-catalyzed dehydration of amide 22 gave the corresponding nitrile in 77% yield. Acid-mediated Boc deprotection allowed the isolation of HCl salts 23-26 in excellent yields. Starting from 2-3 mmol of 2a, useful quantities (50-80 mg) of fragment compounds were rapidly synthesized, highlighting the practical applications of this methodology.