反応 #1068958

ord-b7d7bdaa31024d2f88bbb35879aa4a83

反応方程式

C[C@@H]1CC[C@H]2[C@@H](C)C(=O)O[C@@H]3O[C@]4(C)CC[C@@H]1[C@]32OO4
artemisinin
C=C(C(=O)O)[C@@H]1CC[C@@H](C)[C@@H]2CCC(C)=C[C@@H]21
artemisinic acid
C[C@@H]1CC[C@H]2[C@@H](C)C(=O)O[C@@H]3O[C@]4(C)CC[C@@H]1[C@]32OO4
Compound 3
C[C@@H]1CC[C@H]2[C@@H](C)C(=O)O[C@@H]3O[C@]4(C)CC[C@@H]1[C@]32OO4
artemisinin
C=C(C(=O)O)[C@@H]1CC[C@@H](C)[C@@H]2CCC(C)=C[C@@H]21
Compound 1
C=C(C(=O)O)[C@@H]1CC[C@@H](C)[C@@H]2CCC(C)=C[C@@H]21
artemisinic acid
→
C=C(C(=O)O)[C@@H]1CC[C@@H](C)[C@@H]2CCC(C)=C[C@@H]21
artemisinic acid
C[C@@H]1CC[C@H]2[C@@H](C)C(=O)O[C@@H]3O[C@]4(C)CC[C@@H]1C32O4
desoxyartemisinin

反応物

C[C@@H]1CC[C@H]2[C@@H](C)C(=O)O[C@@H]3O[C@]4(C)CC[C@@H]1[C@]32OO4
artemisinin
C=C(C(=O)O)[C@@H]1CC[C@@H](C)[C@@H]2CCC(C)=C[C@@H]21
artemisinic acid
C[C@@H]1CC[C@H]2[C@@H](C)C(=O)O[C@@H]3O[C@]4(C)CC[C@@H]1[C@]32OO4
Compound 3
C[C@@H]1CC[C@H]2[C@@H](C)C(=O)O[C@@H]3O[C@]4(C)CC[C@@H]1[C@]32OO4
artemisinin
C=C(C(=O)O)[C@@H]1CC[C@@H](C)[C@@H]2CCC(C)=C[C@@H]21
Compound 1
C=C(C(=O)O)[C@@H]1CC[C@@H](C)[C@@H]2CCC(C)=C[C@@H]21
artemisinic acid

試薬

なし

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    その他produced a yield of approximately 7%
  2. 2
    その他for purification of the resulting artemisinin

実験手順

Because there is far more artemisinic acid (Compound 1) than artemisinin (Compound 3) in Artemisia annua, the conversion of the former to the latter has received a great deal of attention. Prior synthetic conversion of 1 to 3 required a greater number of steps, produced a yield of approximately 7% and required the use of column chromatography for purification of the resulting artemisinin. Other attempts to simplify the process resulted in conversion of artemisinic acid into desoxyartemisinin, but did not . result in conversion to artemisinin.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US04992561uspto-grants-1991_02