10.1016/S0957-4166(01)00391-3
The study in the provided scholarly article focuses on the synthesis of specific octahydroquinolin-7-ones, which are compounds derived from aspidosperma alkaloids and are important in asymmetric synthesis. The researchers synthesized the enamine (?)-(1’S)-5-ethyl-1-(1’-phenylethyl)-1,2,3,4-tetrahydropyridine 4 and used it to create (?)-(1’S,4aS,8aR)- and (+)-(1’S,4aR,8aS)-4a-ethyl-1-(1’-phenylethyl)-octahydroquinolin-7-ones 5 and 6. Key chemicals used in the study include (?)-(S)-1-phenylethylamine, 4-formyl-hexanoic acid methyl ester, LiAlH4/THF for reduction, and methyl vinyl ketone (MVK) in the presence of KOH/18-crown-6/methanol. These chemicals served various purposes, such as starting materials for the synthesis, a reducing agent, and reagents for the condensation reaction to form the desired octahydroquinolin-7-ones. The study also reports an X-ray study of compound 6, which confirmed the cis-fused ring structure and absolute configurations of the stereogenic centers. The purpose of these chemical syntheses was to explore the applications of 3,4-dihydro-1H-pyridin-2-ones in asymmetric synthesis and to prepare compounds 5 and 6 with specific stereochemistries.
10.1021/ol991083v
The research focuses on the asymmetric synthesis of (?)-slaframine and its N-acetyl derivative, employing an enantiopure dihydropyridone as a key chiral building block. Slaframine is a metabolite produced by the fungus Rhizoctonia leguminicola, which has been noted for inducing excessive salivation in ruminants upon consumption of contaminated forage. Beyond its role as a mycotoxin, slaframine has shown potential as a drug candidate for treating symptoms associated with cystic fibrosis and diseases arising from cholinergic dysfunctions.
