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. Author manuscript; available in PMC: 2016 Aug 1.
Published in final edited form as: Bioorg Med Chem. 2015 Mar 31;23(15):5061–5074. doi: 10.1016/j.bmc.2015.03.063

Scheme 2.

Scheme 2

Synthesis of fragment 23 for depsipeptide macrocycle. Reagents and conditions: (a) TrtSH, Et3N, CH2Cl2; (b) (formylmethylene)triphenylphosphorane, PhH, 80 ° C, 77% over 2 steps; (c) (R)-1-(4-benzyl-2-thioxothiazolidin-3-yl)ethanone, TiCl4, DIPEA, CH2Cl2, −78 ° C, 76%; (d) 2-(trimethylsilyl)ethanol, imidazole, CH2Cl2, 83%; (e) N-Fmoc-Val-OH, EDCI, DIPEA, DMAP, CH2Cl2, 77%.