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Sonogashira reaction partners for the total synthesis of PD1 and preparation of 221, as reported by Serhan and co-workers [106]. Reagents and conditions: i. nBuLi, BF·OEt2, −78 °C, THF, 84%; ii. TBDPS–Cl, imidazole, DMAP, rt, CH2Cl2, 89%; iii. CSA, rt, CH2Cl2/MeOH, 78%; iv. H2/Lindlar cat., quinoline, rt, EtOAc, 95%; v. DMSO, (COCl)2 Et3N, −78 °C, CH2Cl2, 98%; vi. PPh3, CBr4, 0 °C, CH2Cl2,72%; vii. nBuLi, Et2O, 83%.
