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. 2015 May 11;6(6):707–710. doi: 10.1021/acsmedchemlett.5b00146

Scheme 2. Synthesis of Quinone Trimethyl Locks 5H, 7H, and 8H and Their Methyl Esters.

Scheme 2

Reagents and conditions: (a) Br2, AcOH, rt, 80%; (b) SOCl2, MeOH, reflux, 77%; (c) NaN3, MeOH–H2O, rt, 91%; (d) 1. PPh3, CH2Cl2, rt; 2. AcOH, THF–H2O, reflux, 66% for 2 steps; (e) LiOH, MeOH–H2O, rt, 91%; (f) NBS, CH3CN–H2O–acetone, rt, 79%; (g) H2SO4 (cat.), MeOH, reflux, 95%.