51114-95-5Relevant academic research and scientific papers
Synthesis of C4-C5 cycloalkyl-fused and C6-modified chromans via ortho-quinone methides
Tangdenpaisal, Kassrin,Chuayboonsong, Kanokpish,Sukjarean, Patchaya,Katesampao, Varisa,Noiphrom, Nok,Ruchirawat, Somsak,Ploypradith, Poonsakdi
, p. 1050 - 1064 (2015/03/31)
Starting from 3,5-dimethoxybenzaldehyde, some functionalized 2,3,4-trisubstituted tricyclic 4,5-cycloalkyl-fused and 6-modified chromans could be prepared via ortho-quinone methides (o-QMs)/hetero-Diels-Alder (HDA) reactions of the appropriate precursors.
Intramolecular Friedel-Crafts Acylation Reaction Promoted by 1,1,1,3,3,3-Hexafluoro-2-propanol
Motiwala, Hashim F.,Vekariya, Rakesh H.,Aubé, Jeffrey
supporting information, p. 5484 - 5487 (2015/11/18)
Simple dissolution of an arylalkyl acid chloride in 1,1,1,3,3,3-hexafluoro-2-propanol promotes an intramolecular Friedel-Crafts acylation without additional catalysts or reagents. This reaction is operationally trivial in both execution and product isolation (only requiring concentration followed by purification) and accommodates a broad range of substrates. Preliminary studies that bear upon potential reaction mechanisms are reported.
Synthesis of carbocyclic analogs of dehydroaltenusin: Identification of a stable inhibitor of calf DNA polymerase α
Ková?ová, Silvia,Adla, Santosh Kumar,Maier, Luká?,Babiak, Michal,Mizushina, Yoshiyuki,Paruch, Kamil
, p. 7575 - 7582 (2015/09/07)
Syntheses of carbocyclic analogs of dehydroaltenusin tautomers are reported. Both target compounds, cDHA (2,8-dihydroxy-6-methoxy-10a-methyl-10,10a-dihydrophenanthrene-3,9-dione) and cDHAs (4′,5-dihydroxy-6′-methoxy-2-methylspiro[cyclohexa[2,5]diene-1,1′-
Synthesis of isochroman-3-ylacetates and isochromane-γ-lactones through rearrangement of aryldioxolanylacetates
Giles, Robin G. F.,Rickards, Rodney W.,Senanayake, Badra S.
, p. 3949 - 3956 (2007/10/03)
Lewis acid catalysed rearrangement of methyl 4,5-trans-4-aryldioxolan-5-ylacetates 1 provides a convenient route to substituted methyl isochroman-3-ylacetates 2 and isochromane-γ-lactones 3. The choice of Lewis acid is determined by the substitution pattern of the aromatic ring. The two contiguous isochromane stereocentres are transferred unchanged from the parent dioxolanes, while the configuration of the isochromane methyl group is dependent upon the aryl substitution, the reagent and the reaction conditions. Thus treatment of the C-2 epimeric 3′,5′-dimethoxyphenyldioxolanes 4 and 5 with camphorsulfonic acid afforded a mixture of the C-5 epimeric isochromane lactones 26 and 29, the former being favoured at lower acid concentrations, the latter at higher concentrations. Titanium tetrachloride isomerised the analogous 2′-chloro-5′-methoxyphenyldioxolanes 6 and 7 into the methyl isochroman-3-ylacetate 38, which could be lactonised to the isochromane lactone 27. Phosphoric acid converted the 2′,5′-dimethoxyphenyldioxolanes 8 and 9 into a mixture of the isochromane lactones 28 and 31, while similar treatment of the hydroxylactone 22 in the presence of acetaldehyde afforded the isochromane lactone 28 directly and with complete diastereoselectivity. Oxidative demethylation and annulation of this isochromahe lactone 28 afforded 5-epi-7-deoxykalafungin 41.
