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. Author manuscript; available in PMC: 2016 Mar 12.
Published in final edited form as: J Med Chem. 2015 Feb 18;58(5):2406–2416. doi: 10.1021/jm5019115

Scheme 4a.

Scheme 4a

aReagents and conditions: (i) isobutanol, H2SO4, 120 °C, reflux, 16 h, dark, 79%; (ii) tert-butyl hydroxybutanoate, Ph3P, DIAD, THF, 25 °C, 4 h, dark; (iii) TFA, CH2Cl2, 25 °C, 3 h, dark, 85% over 2 steps; (iv) 2’-TBDMS-paclitaxel, DIC, DMAP, CH2Cl2/DMF, 25 °C, 24 h, dark, 70%; (v) HF/pyridine, CH3CN/pyridine; 0 °C to 25°C, 48 h, dark, 87%.