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. Author manuscript; available in PMC: 2012 Dec 22.
Published in final edited form as: J Med Chem. 2011 Nov 23;54(24):8471–8489. doi: 10.1021/jm201018g

Scheme 6.

Scheme 6

Synthesis of pyrano(2,3b)pyridine analoguesa

R1 = phenyl (20a), cyclohexyl (20b)

a Reagents and Conditions: (a) (i) BuLi, -78 °C (ii). DMF, anh.ether, 31%; (b) R1NH2, ZnCl2, NaCNBH3, MeOH, 49%; (c) 3,4-diethoxybenzenesulfonyl chloride, Et3N, DCM, r.t., 43 – 60%.