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. 2014 Mar 10;136(13):4853–4856. doi: 10.1021/ja5007838

Scheme 1. Synthetic Utility of the Phenylsulfonylated Product.

Scheme 1

Reaction conditions: 7a to 7b, PSMS (6, 3 equiv), TBHP (10 equiv), PhCF3/H2O, rt, 24 h (78%); 7b to 7d, (1) Mg (40 equiv), CD3OD, reflux, 24 h; (2) SmI2 (6 equiv), THF:D2O (10:1), rt, 30 min, 70% (2 steps), 91% D incorporation; 7b to 7e, (1) NaH (10 equiv), NFSI (5 equiv), DMF, 0 °C to rt, 12 h, 94%; (2) Mg (30 equiv), 8 M HOAc:NaOAc (1:1) buffer solution, DMF, rt, 8 h, 73%. 7b to 7f, KOtBu, S8, THF; then MeI (quant.); 7b to 7g, (1) NaH, PhCHO, THF, 50 °C, 36 h; (2) SmI2, rt, 5 min (32%).