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. 2014 Jan 30;53(10):2692–2695. doi: 10.1002/anie.201310164

Scheme 4.

Scheme 4

Completion of leiodermatolide (1). Reagents and conditions: a) [Pd(PPh3)4] (10 mol %), CuTC, Bu4NPh2PO2, DMF, 80 %; b) HF⋅py, pyridine, THF; c) TEMPO, PhI(OAc)2, CH2Cl2; d) NaClO2, NaH2PO4, 2-methyl-2-butene, tBuOH, H2O, THF; e) TBAF, THF, 50 °C, 51 % over 4 steps; f) TCBC, Et3N, THF; DMAP, PhMe, 80 %; g) Dowex 50WX8, MeOH, 91 %; h) TMS-imidazole, CH2Cl2; PPTS, MeOH; Cl3CCONCO, CH2Cl2, −78 °C; Al2O3; PPTS, MeOH, 53 %. DMAP=4-dimethylaminopyridine, py=pyridine, TBAF=tetrabutylammonium fluoride, TC=2-thiophenecarboxylate, TCBC=2,4,6-trichlorobenzoyl chloride, TEMPO=2,2,6,6-tetramethylpiperidine 1-oxyl.