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. Author manuscript; available in PMC: 2020 Feb 1.
Published in final edited form as: Eur J Med Chem. 2018 Nov 23;163:320–332. doi: 10.1016/j.ejmech.2018.11.056

Scheme 1.

Scheme 1.

Synthesis of THF Ring and final coupling to make Des-PSZ Analogue 1. Reagents and conditions: (a) AlCl3, DCM, 45 °C, 3-4 h, 65%; (b) NaOtBu, MePPh3Br, THF, 40 °C, 12 h, 100%; (C) i. DCM, TEA, pivaloyl chloride, ii. OXZ, DMAP, DMF, 45-50 °C, 12 h, 68%; (d) i. DCM, TiCl4, DIPEA, 0 °C, 1 h, ii. s-trioxane, TiCl4, DCM, 0 °C, 12 h, 50%; (e) I2, pyridine, CH3CN, R.T., 20 h, 61%; (f) NaBH4, DMSO, 110°C, 12 h, 62%; (g) Pyridine, TsCl, R.T., 12 h, 100%; (h) Cs2CO3, DMSO, 90 °C, 12 h, 63%.