87322-20-1

Upstream product

• 5113-87-1 3-methyl-6-(prop-1-en-2-yl)cyclohexene 
• 416864-81-8 (3R,3aS,6R,7R,7aR)-(3a,4,5,6,7,7a)-hexahydro-3,6-dimethylbenzofuran-2(3H)-one 
• 503272-14-8 (R)-2-{(1S,2S,3S,4R)-2-Hydroxy-4-methyl-3-[2-(2-methyl-[1,3]dithiolan-2-yl)-ethyl]-cyclohexyl}-propionic acid methyl ester 
• 84051-31-0 (1R,5R)-2-(2-Benzyloxy-1-methyl-ethyl)-5-methyl-cyclohexanol 
• 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 
• 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 
• 93913-62-3 3(R)-methyl-6(S)-<1(R)-methyl-2-(phenylmethoxy)ethyl>-2(S)-(3-oxobutyl)cyclohexanone 
• 93913-64-5 1α,10α-methyl-7β-<2'β-(1'-benzyloxy)-propyl>-decalone-4 
• 93913-65-6 1α-Δ⁴-4,10α-dimethyl-7β-<2'β-(1'-benzyloxy)-propyl>-decalin 
• 13834-07-6 (1R,5R)-2-(2-Hydroxy-1-methyl-ethyl)-5-methyl-cyclohexanol 
• 84051-32-1 (2S,5R)-2-((R)-1-(benzyloxy)propan-2-yl)-5-methylcyclohexanone 
• 103775-34-4 (R)-2-[(1R,2S,3S,4R)-2-Formyl-4-methyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid methyl ester 
• 80286-58-4 artemisinic acid 
• 503272-15-9 (R)-2-{(1S,3S,4R)-4-Methyl-3-[2-(2-methyl-[1,3]dithiolan-2-yl)-ethyl]-2-oxo-cyclohexyl}-propionic acid methyl ester 

Downstream Products

• 63968-64-9 C₁₂H₁₃O₂(CH₃)3(O)(OO) 
• 63968-64-9 arteannuin (Qinghaosu) 

Relevant academic research and scientific papers

Stereoselective total synthesis of (+)-artemisinin

The total synthesis of the novel antimalarial drug, a sesquiterpene endoperoxide, (+)-artemisinin is described. The approach is flexible and stereoselective. The use of an intermolecular radical reaction on an intermediate iodolactone and a Wittig reaction on a ketone were employed for the synthesis.

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.