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. Author manuscript; available in PMC: 2009 Nov 1.
Published in final edited form as: Nat Prod Rep. 2009 Mar 11;26(5):585–601. doi: 10.1039/b813799b

Scheme 12.

Scheme 12

Wipf's end game strategy for disorazole C1. Reagents and conditions: (a) PdCl2(PPh3), CuI, Et3N, CH3CN, −20 °C to rt, 94%; (b) 75, DCC, DMAP, CH2Cl2, 0 °C to rt, 80%; (c) 67, PdCl2(PPh3)2, CuI, Et3N, CH3CN, −20 °C to rt, 94%; (d) 1N LiOH, H2O/THF, 98%; (e) 2,4,6-trichlorobenzoyl chloride, Et3N, THF, then DMAP, toluene, 79%; (f) DDQ, phosphate buffer (pH 6.7), CH2Cl2, 61%; (g) H2, Lindlar's catalyst, quinoline, EtOAc, 57%.