6018-41-3Relevant articles and documents
Diels-Alder reaction of 1-methylcycloprop-2-ene-1-carbonitrile with methyl 2-Oxo-2H-pyran-5-carboxylate
Plemenkov,Ashirov,Lodochnikova,Litvinov,Zagidullin
, p. 969 - 972 (2006)
The Diels-Alder reaction of 1-methylcycloprop-2-ene-1-carbonitrile and coumalic acid methyl ester (methyl 2-oxo-2H-pyran-5-carboxylate) gave a 2:1 adduct with endo-syn configuration of both cyclopropane fragments, which was established by X-ray analysis. According to the 1H NMR data, the reaction involves intermediate formation of decarboxylated 1:1 adduct having a cycloheptatriene structure; its isomerization into the corresponding caradiene, followed by addition of the second dienophile molecule, was confirmed by quantum-chemical calculations. Pleiades Publishing, Inc., 2006.
Stereoselective construction of a key hydroindole precursor of epidithiodiketopiperazine (ETP) natural products
Feng, Minghao,Jiang, Xuefeng
supporting information, p. 9690 - 9692 (2014/08/18)
An asymmetric synthetic strategy for constructing the divergent-synthesis monomer of epidithiodiketopiperazine (ETP) natural products has been successfully developed. The functionalized 2,3,3a,4,7,7a-hexahydroindole scaffold was constructed by a diastereoselective inverse electron-demand Diels-Alder (IEDDA) reaction. This journal is the Partner Organisations 2014.
Homosecoiridoid alkaloids with amino acid units from the flower buds of lonicera japonica
Yu, Yang,Zhu, Chenggen,Wang, Sujuan,Song, Weixia,Yang, Yongchun,Shi, Jiangong
, p. 2226 - 2233 (2014/01/17)
Nine new homosecoiridoid alkaloids, named lonijaposides O-W (1-9), along with 19 known compounds, were isolated from an aqueous extract of the flower buds of Lonicera japonica. Their structures and absolute configurations were determined by spectroscopic data analysis and chemical methods. Lonijaposides O-W have structural features that involve amino acid units sharing the N atom with a pyridinium (1-5) or nicotinic acid (6-9) moiety. The absolute configurations of the amino acid units were determined by oxidation of each pyridinium ring moiety with potassium ferricyanide, hydrolysis of the oxidation product, and Marfey's analysis of the hydrolysate. This procedure was validated by oxidizing and hydrolyzing synthetic model compounds. The phenylalanine units in compounds 4, 5, and 9 have the d-configuration, and the other amino acid units in 1-3 and 6-8 possess the l-configuration. Compounds 1, 4, 6, and 9 and the known compounds 3,4-di-O-caffeoylquinic acid, 3,5-di-O-caffeoylquinic acid, and 5′-O-methyladenosine exhibited antiviral activity against the influenza virus A/Hanfang/359/95 (H3N2) with IC50 values of 3.4-11.6 μM, and 4 inhibited Coxsackie virus B3 replication with an IC50 value of 12.3 μM.