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Hoffmann's synthesis of a masked northern half of disorazole D1. Reagents and conditions: (a) NaH, TBDMSCl, THF, 85%; (b) SO3·Pyr, Et3N, DMSO/CH2Cl2, 0 °C, 96%; (c) CrCl2, CHI3, THF, 72%; (d) 90, PdCl2(PPh3)2, CuI, Et3N, DMF, 86%; (e) TBAF, THF, 0 °C, 99%; (f) Dess–Martin periodinane, pyridine, CH2Cl2, 0 °C, 75%; (g) 86, LiHMDS, HMPA, THF, −78 °C to rt, 32%.
