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. Author manuscript; available in PMC: 2012 Feb 1.
Published in final edited form as: Nat Chem. 2011 Jun 19;3(8):615–619. doi: 10.1038/nchem.1074

Figure 3. Completion of des-epoxy- and C6,C7-epi-yuanhuapin.

Figure 3

Conditions: (a) K2CO3, MeOH/H2O, 50 °C, 76%; (b) TBS-OTf, 2,6-lutidine, CH2Cl2, 0 °C, 97%; (c) Li-naphthalenide, THF, −30 °C, 88%; (d) triphosgene, pyridine, CH2Cl2, r.t., 94%; (e) 4:1:1 AcOH:THF:H2O, r.t., 82%; (f) Tf2O, 2,6-lutidine, CH2Cl2, −78 °C; (g) TBAI, CH3CN, 65 °C, 93% (two steps); (h) Zn, NH4Cl, EtOH, 160°C, microwave, 77%; (i) 2,2-dimethoxypropane, PPTS, CH2Cl2, 40 °C, 86%; (j) NBS, (BzO)2, NaHCO3, CCl4/PhH, 70 °C; (k) KOAc, 18-crown-6, CH3CN, r.t., 52% (two steps, 39% RSM); (l) LAH, THF, 0 °C to r.t., 75%; (m) BzCl, DMAP, Et3N, CH2Cl2, r.t., 90%; (n) p-TsOH, MeOH, DMF, 200 °C, microwave, 49% (11% RSM); (o) Ac2O, DMAP, CH2Cl2, r.t., 90%; (p) TAS-F, DMF, r.t., 89%; (q) IBX, DMSO/PhCH3, 70 °C, 97%; (r) K2CO3, MeOH, r.t.; (s) LiBF4, H2O/CH3CN, 70 °C, 29% (two steps); (t) VO(OiPr)3, t-BuOOH, (1S,2S)-N,N′-dihydroxy-N,N′-bis(3,3,3-triphenylpropionyl)-1,2-cyclohexadiamine, CH2Cl2/PhH, 4 °C, 81%.