Potassium Peroxymonosulfate [> ca. 45%(T) as KHSO₅]

• Potassium Peroxymonosulfate [> ca. 45%(T) as KHSO₅] [O0310]
• Methanol

To a solution of compound 1 (0.10 g, 0.34 mmol) in methanol (3.0 mL) was added potassium peroxymonosulfate (3.9 g, 6.3 mmol) at ambient temperature and stirred at 60 °C for 40 hours. The mixture was added water (30 mL) and extracted with ethyl acetate (30 mL x 3). The organic phase was dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by column chromatography (ethyl acetate:hexane = 1:19 on silica gel) to give compound 2 as a white solid.

The reaction mixture was monitored by UPLC
Since the reaction mixture turns to acidic, there is a possibility of decomposition when applied to acid-unstable compounds.

compound 2

¹H NMR (400 MHz, CDCl₃); δ 7.74-7.54 (m, 5H), 7.38-7.16 (m, 5H), 3.75-3.66 (m, 2H), 2.84 (t, J = 7.3 Hz, 2H), 2.38-2.24 (m, 2H).

• Total Synthesis of the GRP78-Downregulatory Macrolide (+)-Prunustatin A, the Immunosuppressant (+)-SW-163A, and a JBIR04 Diastereoisomer That Confirms JBIR-04 Has Nonidentical Stereochemistry to (+)-Prunustatin A
• S. Manaviazar, P. Nockemann, K. J. Hale, Org. Lett. 2016, 18, 2902.