Asymmetric synthesis of febrifugine and isofebrifugine using yeast reduction

被引:39
|
作者
Takeuchi, Y [1 ]
Azuma, K [1 ]
Takakura, K [1 ]
Abe, H [1 ]
Harayama, T [1 ]
机构
[1] Okayama Univ, Fac Pharmaceut Sci, Okayama 7008530, Japan
关键词
D O I
10.1039/b005028h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The antimalarial agents febrifugine ((+)-1) and isofebrifugine ((+)-2) were asymmetrically synthesized from chiral piperidin-3-ol ((+)-4), which was prepared by the reductive dynamic optical resolution of the 3-piperidone derivatives ((+/-)-3) using baker's yeast.
引用
收藏
页码:1643 / 1644
页数:2
相关论文
共 50 条
  • [1] Asymmetric synthesis of (+)-febrifugine and (+)-isofebrifugine using yeast reduction
    Takeuchi, Y
    Azuma, K
    Takakura, K
    Abe, H
    Kim, HS
    Wataya, Y
    Harayama, T
    TETRAHEDRON, 2001, 57 (07) : 1213 - 1218
  • [2] Catalytic asymmetric synthesis of febrifugine and isofebrifugine
    Kobayashi, S
    Ueno, M
    Suzuki, R
    Ishitani, H
    TETRAHEDRON LETTERS, 1999, 40 (11) : 2175 - 2178
  • [3] Asymmetric synthesis of antimalarial alkaloids (+)-febrifugine and (+)-isofebrifugine
    Huang, PQ
    Wei, BG
    Ruan, YP
    SYNLETT, 2003, (11) : 1663 - 1667
  • [4] Catalytic asymmetric synthesis of antimalarial alkaloids febrifugine and isofebrifugine and their biological activity
    Kobayashi, S
    Ueno, M
    Suzuki, R
    Ishitani, H
    Kim, HS
    Wataya, Y
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (18): : 6833 - 6841
  • [5] THE STRUCTURE OF FEBRIFUGINE AND ISOFEBRIFUGINE
    KOEPFLI, JB
    BROCKMAN, JA
    MOFFAT, J
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (07) : 3323 - 3323
  • [6] Total synthesis of dl-febrifugine and dl-isofebrifugine
    Takeuchi, Y
    Abe, H
    Harayama, T
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1999, 47 (06) : 905 - 906
  • [7] Synthesis of D/L-febrifugine and D/L-isofebrifugine
    Takeuchi, Y
    Hattori, M
    Abe, H
    Harayama, T
    SYNTHESIS-STUTTGART, 1999, (10): : 1814 - 1818
  • [8] AN ANTIMALARIAL ALKALOID FROM HYDRANGEA .21. SYNTHESIS AND STRUCTURE OF FEBRIFUGINE AND ISOFEBRIFUGINE
    BAKER, BR
    MCEVOY, FJ
    SCHAUB, RE
    JOSEPH, JP
    WILLIAMS, JH
    JOURNAL OF ORGANIC CHEMISTRY, 1953, 18 (02): : 178 - 183
  • [9] An asymmetric synthesis of febrifugine, halofuginone and hemiketal isomers
    Smullen, Shaun
    Evans, Paul
    TETRAHEDRON, 2017, 73 (37) : 5493 - 5499
  • [10] Concise Asymmetric Synthesis of Antimalarial Alkaloid (+)-Febrifugine
    Wang, Rui
    Fang, Kai
    Sun, Bing-Feng
    Xu, Ming-Hua
    Lin, Guo-Qiang
    SYNLETT, 2009, (14) : 2301 - 2304