87206-33-5

Usage

Uses

Used in Pharmaceutical Industry:
(1aR,4R,4aS,7R,7aS,9aR)-4,7,9a-trimethyldecahydro-3H-oxireno[7,8]naphtho[8a,1-b]furan-3-one is used as a potential pharmaceutical candidate for its possible biological activity due to its unique structure and functional groups. It may be studied for its potential medicinal properties, such as treating specific diseases or conditions.
Used in Organic Synthesis:
(1aR,4R,4aS,7R,7aS,9aR)-4,7,9a-trimethyldecahydro-3H-oxireno[7,8]naphtho[8a,1-b]furan-3-one is used as a starting material in organic synthesis for the development of other organic compounds. Its unique carbon skeleton and functional groups make it a valuable component in creating new molecules with potential applications in various fields, such as materials science, pharmaceuticals, or agrochemicals.

Upstream product

• 85031-60-3 4α-hydroperoxy-amorph-5-en-12-oic acid 
• 50906-56-4 (1R,5S,8R,9S,12R,14R)-8,12-dimethyl-4-methylidene-2,13-dioxatetracyclo[7.5.0.0^1,5.0^12,14]tetradecan-3-one 

Downstream Products

• 63968-64-9 (+)-artemisinin 
• 141039-67-0 2-(2-(3-((2R)-methoxymethylcarbonylpropyl)-2-methoxymethyloxymethylene-(6R)-methylcyclohex-(1S)-yl)ethyl)-2-methyl-1,3-dioxolane 
• 141039-66-9 2-(2-(3-(3-hydroxy-(2R)-methylpropyl)-2-methoxymethoxymethylene-(6R)-methylcyclohex-(1S)-yl)ethyl)-2-methyl-1,3-dioxolane 
• 126189-95-5 (+)-deoxyartemisinin 
• 63968-64-9 C₁₂H₁₃O₂(CH₃)3(O)(OO) 

Relevant academic research and scientific papers

The mechanism of the spontaneous autoxidation of dihydroartemisinic acid

Dihydroartemisinic acid undergoes slow spontaneous autoxidation to artemisinin and other natural products, which have been reported from the medicinal plant Artemisia annua. The mechanism of this complex transformation is shown to involve four steps: (i) initial reaction of the Δ4.5-double bond of dihydroartemisinic acid with molecular oxygen, (ii) Hock cleavage of the resulting tertiary allylic hydroperoxide; (iii) oxygenation of the enol product from Hock cleavage; and (iv) cyclization of the resulting vicinal hydroperoxyl-aldehyde to the 1,2,4-trioxane system of artemisinin.

Synthesis of (+)-Artemisinin and (+)-Deoxoartemisinin from arteannuin B and arteannuic acid

(+)-Artemisinin and (+)-Deoxoartemisinin were prepared for the first time from arteannuin B. The synthetic route is short and efficient, making use of the prior art for the final photo-oxygenation/cyclization reaction. A convergent route to each of the above-named products from arteannuic acid is also described. A novel oxidative lactonization reaction was developed for this sequence.