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Hoffmann's 2nd generation synthesis of a masked triene monomer of disorazole C1. Reagents and conditions: (a) (ClCO)2, Et3N, DMSO/CH2Cl2, −78 °C to −40 °C, then 56, K2CO3, MeOH, 0 °C to rt, 75% (over 2 steps); (b) n-Bu3SnH, Pd(PPh3)4, THF, then I2, 88%; (c) TMS-acetylene, PdCl2(PPh3)2, CuI, Et3N, CH3CN, 99%; (d) TBAF (1.1 equiv), THF, 0 °C to rt, 81%; (e) TBAF (10.0 equiv), THF, 95%; (f) PdCl2(PPh3)2, CuI, Et3N, DMF, 89%.
