103775-34-4

Upstream product

• 186581-53-3 diazomethane 
• 105250-95-1 (R)-2-[(1R,2S,3S,4R)-2-Formyl-4-methyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid 
• 87391-99-9 2-(4,7-dimethyl-(1α-H),2,3,(4β-H),(4aα-H),5,6,(8aα-H)-octahydronaphthalen-1-yl)propionic acid methyl ester 
• 85031-63-6 5α-hydroperoxy-amorph-5-en-12-oic acid methyl ester 
• 85031-59-0 dihydroartemisinic acid 
• 80286-58-4 artemisinic acid 
• 84051-32-1 (2S,5R)-2-((R)-1-(benzyloxy)propan-2-yl)-5-methylcyclohexanone 
• 13834-07-6 (1R,5R)-2-(2-Hydroxy-1-methyl-ethyl)-5-methyl-cyclohexanol 
• 84051-31-0 (1R,5R)-2-(2-Benzyloxy-1-methyl-ethyl)-5-methyl-cyclohexanol 
• 93913-65-6 1α-Δ⁴-4,10α-dimethyl-7β-<2'β-(1'-benzyloxy)-propyl>-decalin 
• 93913-64-5 1α,10α-methyl-7β-<2'β-(1'-benzyloxy)-propyl>-decalone-4 
• 93913-62-3 3(R)-methyl-6(S)-<1(R)-methyl-2-(phenylmethoxy)ethyl>-2(S)-(3-oxobutyl)cyclohexanone 
• 93913-63-4 1α-Δ⁵-10α-methyl-7β-<2'β-(1'-benzyloxy)-propyl>-decalone-4 
• 129145-25-1 (3aS,6R,6aS,9R,9aS,9bS)-3,6,9-Trimethyl-dodecahydro-benzo[de]chromen-9-ol 

Downstream Products

• 63968-64-9 arteannuin (Qinghaosu) 
• 87322-20-1 (R)-2-[(1S,3S,4R)-2-[1-Methoxy-meth-(Z)-ylidene]-4-methyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid methyl ester 
• 87322-21-2 (R)-2-{(1S,3S,4R)-2-[1-Methoxy-meth-(Z)-ylidene]-4-methyl-3-[2-(2-methyl-[1,3]dithian-2-yl)-ethyl]-cyclohexyl}-propionic acid methyl ester 
• 106623-24-9 (R)-2-{(1R,2S,3S,4R)-2-Formyl-4-methyl-3-[2-(2-methyl-[1,3]dithian-2-yl)-ethyl]-cyclohexyl}-propionic acid methyl ester 

Relevant academic research and scientific papers

The role of the 12-carboxylic acid group in the spontaneous autoxidation of dihydroartemisinic acid

Three of the four steps in the slow spontaneous autoxidation of dihydroartemisinic acid to artemisinin ('ene-type' reaction of molecular oxygen with the Δ4,5 double bond, Hock cleavage of the resulting tertiary allylic hydroperoxide, oxygenation of the enol product from Hock cleavage and cyclization of the resulting vicinal hydroperoxyl-aldehyde to the 1,2,4-trioxane system of artemisinin) are shown to be assisted by the proximity of the 12-carboxylic acid functional group in dihydroartemisinic acid to the functional groups participating in these reactions.

Stereoselective synthesis of artemisinin

A stereoselective synthesis of artemisinin 11 based on intramolecular Diels-Alder reaction of the triene 4 derived from (+)isolimonene 2 is described.

TOTAL SYNTHESIS OF ARTEANNUIN AND DEOXYARTEANNUIN

Arteannuin 1 is a new sesquiterpene lactone containing a peroxide linkage and is an antimalarial principle isolated from Artemisia annua L. .R(+)-Citronellal 5 as a starting material for the total synthesis was converted into 11R(-)-methyl dihydroarteannuinate 12 in 14 steps.The key intermediate 4 was obtained from compound 12 in 5 steps.The introduction of hydroperoxide in 4 by photooxidation followed by acid treatment gave 1.Hydroxylation of 4 with osmium tetraoxide afforded deoxyarteannuin 2.