76280-92-7

Usage

Uses

Used in Pharmaceutical Industry:
(S)-(+)-Kjellmanianone is used as a potential anticancer agent for its moderate cytotoxicity against various cancer cell lines, including lung, colon, and breast cancer cells. Its ability to target and inhibit the growth of cancer cells makes it a valuable compound for further research and development in the fight against cancer.
Used in Antifungal Applications:
(S)-(+)-Kjellmanianone is used as an antifungal agent due to its demonstrated activity against several species of fungi. This property suggests its potential use in the development of new antifungal medications, which could be beneficial in treating various fungal infections and combating drug-resistant strains.
Used in Research and Development:
(S)-(+)-Kjellmanianone is used as a subject of study in the field of medical and pharmaceutical research. Its unique properties and potential applications make it an interesting molecule for scientists to explore, with the aim of understanding its mechanisms of action and identifying new ways to harness its benefits in the development of novel therapeutic agents.

InChI:InChI=1/C8H10O5/c1-12-5-3-6(9)8(11,4-5)7(10)13-2/h3,11H,4H2,1-2H3/t8-/m1/s1

Upstream product

• 141693-19-8 methyl (+/-)-4-methoxy-2-oxo-3-cyclopentene-1-carboxylate 
• 1407512-42-8 C₁₅H₁₆O₃S 
• 1407512-44-0 C₂₀H₂₅NO₆S 
• 67-56-1 methanol 
• 1407512-45-1 C₁₅H₁₆O₄S 

Relevant academic research and scientific papers

Diterpenoid alkaloid lappaconine derivative catalyzed asymmetric α-hydroxylation of β-dicarbonyl compounds with hydrogen peroxide

A new framework derived from the commercially available diterpenoid alkaloid lappaconitine was evaluated as a Bronsted base catalyst for the enantioselective α-hydroxylation of β-dicarbonyl compounds by using 30% hydrogen peroxide as a green and highly practical source of oxygen. This protocol allows convenient access to the corresponding α-hydroxy-β- oxo esters, α-hydroxy-β-oxo amides and (-)-kjellmanianone with up to 98% yield and 92% ee. Copyright

Catalytic enantioselective O -nitrosocarbonyl aldol reaction of β-dicarbonyl compounds

The first example of a Cu-catalyzed asymmetric O-nitrosocarbonyl aldol reaction is described. This novel protocol allows convenient access to highly enantioenriched α-hydroxy-β-ketoesters including the antibacterial natural product kjellmanianone (up to 99% ee). MnO2 was introduced as a mild efficient oxidant for the in situ generation of nitrosocarbonyl species from hydroxamic acid derivatives.

ENANTIOSELECTIVE SYNTHESIS OF (+)-KJELLMANIANONE

An asymmetric synthesis of the highly oxygenated cyclopentanoid antibiotic (+)-kjellmanianone (1) has been achieved.The key step entailed enantioselective hydroxylation of the prochiral sodium enolate of β-keto ester 2 with the new, enatiomerically pure N-sulfonyloxaziridine 7b, affording 1 in 68.5percent ee (60percent yield).Possible transition state structures for the asymmetric oxidation are evaluated.