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. Author manuscript; available in PMC: 2009 Feb 15.
Published in final edited form as: Bioorg Med Chem. 2007 Nov 6;16(4):1832–1841. doi: 10.1016/j.bmc.2007.11.009

Scheme 1.

Scheme 1

Synthesis of 8-heterobicyclo[3.2.1]octanes. Reagents and conditions: (i) (a) NaN(TMS)2; (b) (1S)-Camphanyl chloride, (c) Recrystallization from CH2Cl2 or THF/hexanes, 64%; (d) NaOCH3,MeOH, 90%; (ii) NaN(TMS)2, PhN(Tf)2, 75%; (iii) 3,4-Cl2-PhB(OH)2, Pd(PPh3)4,LiCl, Na2CO3, 74−96%; (iv) Sml2, THF, MeOH, −60°C, 20%; (v) LiAlH4, THF, −78°C, 85−95%. See: Pjam-Huu et al. Bioorg. & Med. Chem. 15, 1067, 2007; Meltzer et al. J. Med. Chem. 40, 2661, 1997.