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. Author manuscript; available in PMC: 2012 Oct 13.

Published in final edited form as: J Med Chem. 2011 Aug 31;54(19):6786–6795. doi: 10.1021/jm2006904

Scheme 3a — ^aReagents and conditions: (i) a) p-NO₂PhOC(O)Cl, pyridine, CH₂Cl₂, 2h, b) NaN₃, acetone:H₂O, 4d, (R)-3 (80% two steps), (S)-3 (80% two steps); (ii) sealed tube, CH₂Cl₂, 109 °C, (4S,5R)-4 (55%), (4R,5S)-4 (55%); (iii) N-phenyl piperazine, CH₂Cl₂, 2h, (4S,5R)-9 (91%), (4R,5S)-9 (86%); (iv) HCl, EtOAc, 30 min, (4S,5R)-10 (93%), (4R,5S)-10 (92%).