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. Author manuscript; available in PMC: 2016 Jul 23.
Published in final edited form as: J Med Chem. 2015 Jul 9;58(14):5459–5475. doi: 10.1021/acs.jmedchem.5b00391

Scheme 2. a. Synthesis of 4–8.

Scheme 2

aReaction conditions: (a) 29, PPh3, DIAD, THF, 0 °C to rt, 16 h, 15=96%, 24=91%, 27=89%; (b) i)30, CH2Cl2, rt, 14 h; ii) then H2, Pd/C, MeOH–THF, rt, 22 h, 21=62%; (c) 31, Cs2CO3, DMF, 0 °C to rt, 16 h, 16=60%, 22=43%; (d) i)32, CDI, THF, 60 °C, 2 h; ii) then 15, Cs2CO3, THF, rt, 16 h, 17=55%; (e) H2, Pd/C, MeOH, rt, 2 h; (f) 80% aqueous TFA, 0 °C to rt, 4 h, 4=65%, 5=34% (2 steps from 17), 6=61%, 7=18% (2 steps from 24), 8=38 % (2 steps from 27); (g) DPPA, NaN3, 15-crown-5, THF, 0 °C to rt, 4.5 h; (h) H2, Pd/C, MeOH, rt, 20=44%, (2 steps from 19). Nonstandard abbreviations: IPK = isopropylidene ketal.