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. Author manuscript; available in PMC: 2014 May 1.
Published in final edited form as: Medchemcomm. 2013 Mar 12;4(5):822–826. doi: 10.1039/C3MD00021D

Scheme 2.

Scheme 2

Synthesis for compounds 7 and epi-6. Reagents and conditions: (a) acetone, cat. H2SO4, 85%; (b) TBDPSCl, Et3N, 4-dimethylaminopyridine, DMF, 98%; (c) Ph3PMeBr, t-BuOK, THF, 92%; (d) SO3·Py, Et3N, CH2Cl2, 97%; (e) CH2=CHMgBr, THF, −78 °C, 93%; (f) 2nd generation Grubbs catalyst (5 mmol%), CH2Cl2, reflux, 95%; (g) PDC, 4 Å molecular sieve, DMF, 87%; (h) NaBH4, CeCl3·7H2O, MeOH, 0 oC, 98%; (i) 6-chloropurine, Ph3P, DIAD, THF, 95%; (j) 7 M NH3 in MeOH, 100 °C; (k) tetrabutylammonium fluoride, THF, 93% for two steps; (l) H2, 10% Pd/C, MeOH, 91%.