Bennasar, M.-Lluiesa; Zulaica, Ester; Juan, Cecilia; Alonso, Yolanda; Bosch, Joan published the artcile< Addition of Ester Enolates to N-Alkyl-2-fluoropyridinium Salts: Total Synthesis of (±)-20-Deoxycamptothecin and (+)-Camptothecin>, Related Products of 131747-55-2, the main research area is ester enolate addition fluoropyridinium salt; deoxycamptothecin total synthesis; camptothecin total synthesis.
Several 4-substituted dihydropyridones or 2-pyridones have been prepared by nucleophilic addition of α-(methylsulfanyl)ester enolates to N-alkyl-2-fluoropyridinium salts, followed by acid hydrolysis or oxidation with concomitant hydrolysis, of the intermediate 2-fluoro-1,4-dihydropyridine adducts, resp. Addition of the enolate derived from iso-Pr α-(methylsulfanyl)butyrate to N-(quinolylmethyl)-2-fluoropyridinium triflate followed by DDQ treatment gave a pyridone I, from which (±)-20-deoxycamptothecin a known precursor of camptothecin was synthesized by a radical cyclization-desulfurization, with subsequent elaboration of the lactone E ring by chemoselective reduction A similar sequence starting from the enolate of a chiral 2-hydroxybutyric acid derivative (II) provides access to natural (+)-camptothecin.
Journal of Organic Chemistry published new progress about Addition reaction. 131747-55-2 belongs to class pyridine-derivatives, and the molecular formula is C6H6FNO, Related Products of 131747-55-2.