Synthesis of 6α- and 6β-Hydroxydeoxycholic Acid
- Corresponding author: Xu Liang, liangxu@scu.edu.cn
Citation:
Niu Wei, Xiao Dan, Cheng Hang, Xu Liang. Synthesis of 6α- and 6β-Hydroxydeoxycholic Acid[J]. Chinese Journal of Organic Chemistry,
;2020, 40(7): 2114-2119.
doi:
10.6023/cjoc202002008
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Reagents and conditions: (a) NBS, NaHCO3, acetone/H2O, r.t.~85 ℃, 95%; (b) MeOH, PTSA, reflux, 2 h, 100%; (c) TBSOTf, 2, 6-lutidine, DCM, r.t., 96%; (d) mCPBA, NaHCO3, DCM, 48%; (e) CH3CHO, BF3•Et2O, DCM, -78 ℃, 84%; (f) NaBH4, THF/MeOH (V:V=1:1), 0 ℃, 86%; (g) Ac2O, DMAP, pyridine, 80 ℃, 94%; (h) O3, DCM, -78 ℃, then Me2S, r.t., 85%; (i) SmI2, THF/MeOH (V:V=10:1), r.t., 88%; (j) t-BuNH2•BH3, DCM, r.t., then HCl/MeOH, 0 ℃, 46% for 15, 46% for 16; (k) LiOH, THF/MeOH/H2O (V:V:V=5:3:2), 90%.