Enantioselective Synthesis of Core Structures of Hydramicromelins A, B and C
- Corresponding author: Yang Hua, yanghua@zzu.edu.c Liu Hongmin, liuhm@zzu.edu.cn
Citation:
Sun Moran, Dai Lei, Yang Hua, Liu Hongmin, Yu Dequan. Enantioselective Synthesis of Core Structures of Hydramicromelins A, B and C[J]. Chinese Journal of Organic Chemistry,
;2018, 38(9): 2443-2449.
doi:
10.6023/cjoc201802017
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Reagents and conditions: (a) (ⅰ) NaClO, TEMPO, KBr, NaHCO3, DCM-H2O, 5 ℃, 0.5 h; (ⅱ) 2, DCM, r.t., 0.5 h, two steps, 76%. (b) (ⅰ) TFA, DCM, reflux, 3 h; (ⅱ) BnBr, K2CO3, CH3CN, r.t., 12 h, two steps, 83%. (c) m-CPBA, DCM, r.t., 5 min. (d) Zn, HOAC-HCl, r.t., 0.5 h, two steps, 60%.
Reagents and conditions: (a) (ⅰ) H2, Pd/C, MeOH, r.t., 12 h, 94%; (ⅱ) K2CO3, EtOH, r.t., 12 h, 94%. (b) aq.KMnO4, acetone, 5 ℃, 5 min, 43%. (c) (ⅰ) aq. KMnO4, acetone, 5 ℃, 5 min; (ⅱ) TsOH, DCM, r.t., 12 h, 10% 7a, 60% 9. (d) H2, Pd/C or Raney Ni
Reagents and conditions: (a) m-CPBA, DCM, ice bath, 2 h, 70%. (b) (ⅰ) LiOH, THF-H2O (V:V=1:1), r.t., 50 min; (ⅱ) 10% H2SO4, THF-H2O (V:V=1:1), r.t., 2 h, two steps, 65%~70%.