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. Author manuscript; available in PMC: 2016 Nov 2.
Published in final edited form as: J Med Chem. 2016 Jan 25;59(3):892–913. doi: 10.1021/acs.jmedchem.5b01305

Scheme 4. Synthesis of Compounds 3-(RS), 3-(R), 3-(S), 4-(R), and 4-(S)a.

Scheme 4

aReagents and conditions: (i) TBSCl, imidazole, DCM, rt, overnight, 84%; (ii) 41a, NaH, DMF, rt, 2 h, 49%; (iii) HCl, MeOH, rt, 4 h; (iv) TBDPSCl, imidazole, DCM, rt, 1 h; (v) NaH, MeI, THF, rt, 1 h, 11% (3 steps); (vi) NBS, AIBN, CCl4, reflux, 2 h; (vii) 39, DIEA, DCM, 5 h; (vii) HCl, MeOH, rt, 1 h, 24–58% (3 steps).