1316889-31-2

Upstream product

• 103740-01-8 (R)-2-[(1S,3S,4R)-4-Methyl-2-oxo-3-(3-oxo-butyl)-cyclohexyl]-propionic acid methyl ester 
• 95851-75-5 (R)-methyl 2-((3R,6R,9aR)-9a-formyl-3-methoxy-3,6-dimethyloctahydro-3H-benzo[c][1,2]dioxepin-9-yl)propanoate 
• 63968-64-9 C₁₂H₁₃O₂(CH₃)3(O)(OO) 
• 111399-02-1 (3R,3aS,6R,7S,7aS)-3,6-dimethyl-7a-formyl-7-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-hexahydrobenzo[1,2-b]furan-2(3H)-one 
• 1316889-30-1 C₁₇H₂₈O₅ 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 1316889-29-8 C₁₇H₃₂O₆ 
• 63968-64-9 artemisinin 
• 63968-64-9 C₁₂H₁₃O₂(CH₃)3(O)(OO) 
• 126189-95-5 (+)-deoxyartemisinin 
• 1352060-87-7 C₂₃H₄₆O₆Si 

Relevant academic research and scientific papers

Potent antimalarial 1,2,4-trioxanes through perhydrolysis of epoxides

Perhydrolysis of a sterically congested multifunctional epoxide was achieved in ethereal H2O2 with the aid of a recently developed Mo catalyst. The resulting hydroperoxide cyclized to give a 1,2,4-trioxane, which could be readily elaborated into qinghaosu and a range of novel analogues. Some of the compounds with two such trioxane moieties showed in vitro antimalarial activity comparable to or even better than that of artesunate or chloroquine. Molybdenum magic: Facile perhydrolysis of a highly hindered epoxide was achieved with the aid of a molybdenum catalyst. The resulting hydroperoxide was readily converted into a 1,2,4-trioxane, from which natural qinghaosu (QHS, or artemisinin; see scheme) and a range of analogues were constructed. Some of the newly accessed trioxanes showed in vitro antimalarial activity comparable to or even better than that of chloroquine and artesunate. Copyright

A hydrogen peroxide based access to qinghaosu (artemisinin)

Attachment of H2O2 onto the highly hindered quaternary C-12a in an advanced qinghaosu (artemisinin) precursor has been achieved through a facile perhydrolysis of a spiro epoxy ring with the aid of a previously unknown molybdenum species without involving any special equipment or complicated operations. The resultant β-hydroxyhydroperoxide can be further elaborated into qinghaosu, illustrating an entry fundamentally different from the existing ones to this outstanding natural product of great importance in malaria chemotherapy.