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. Author manuscript; available in PMC: 2013 Jul 29.
Published in final edited form as: Bioorg Med Chem Lett. 2010 May 4;20(12):3584–3587. doi: 10.1016/j.bmcl.2010.04.117

Scheme 3.

Scheme 3

Reagents and conditions for the attempted synthesis of 3. (a) NaBH4-LiCl, DME-H2O (6:1), 50 °C, 12 h, 70%.; (b) TsCl, 2,6-lutidine, CH2Cl2, 8 h, 90%.; (c) 3-picoline (2 equiv.), LDA (2 equiv), THF, −78 °C to rt. (d). SOCl2, DMSO, CH2Cl2, −78 °C, 15 min. then Et3N, 15 min. (e) DMSO, DCC, CH2Cl2, 0 °C, 10 min. NOEs considered as proof of relative configuration are depicted as biheaded arrows.