Qing Hau Sau → Artemisinic Acid

HRID 981776

Reaction equation

[CH3:1][C@H:2]1[C@@H:7]2[CH2:8][CH2:9][C:10]([CH3:12])=[CH:11][C@@H:6]2[C@H:5]([C:13]([C:15]([OH:17])=[O:16])=[CH2:14])[CH2:4][CH2:3]1.[CH3:18][C@H:19]1[C@@H:29]2[CH2:30][CH2:31][C@:32]3([CH3:36])O[O:35][C@:28]42[C@H:22]([C@@H:23]([CH3:37])[C:24]([O:26][C@@H:27]4[O:33]3)=[O:25])[CH2:21][CH2:20]1>>[CH3:1][C@H:2]1[C@@H:7]2[CH2:8][CH2:9][C:10]([CH3:12])=[CH:11][C@@H:6]2[C@H:5]([C:13]([C:15]([OH:17])=[O:16])=[CH2:14])[CH2:4][CH2:3]1.[CH3:18][C@H:19]1[C@@H:29]2[CH2:30][CH2:31][C@:32]3([CH3:36])[O:35][C:28]42[C@H:22]([C@@H:23]([CH3:37])[C:24]([O:26][C@@H:27]4[O:33]3)=[O:25])[CH2:21][CH2:20]1

Participants

Reactant 2

HCID 9838675Qing Hau Sau2×

HCID 10922465Artemisinic Acid2×

Product 2

HCID 10922465Artemisinic Acid

HCID 45038803Desoxyartemisinin

Procedure

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.

Workup

customproduced a yield of approximately 7%
customfor purification of the resulting artemisinin

Sources & evidence

ORD record: ord-b7d7bdaa31024d2f88bbb35879aa4a83
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04992561

Linked notes

Loading…