Efficient and selective photogeneration of cholesterol-derived radicals by intramolecular hydrogen abstraction in model dyads.
Three model dyads have been synthesized by esterification of beta- and alpha-cholesterol (Ch) with (S)- and/or (R)-ketoprofen (Kp). The alpha-dyads are efficient photogenerators of the 7-allyl Ch radicals by intramolecular H abstraction. Subsequent cyclization via C-C coupling occurs in a stereoselective way.
Andreu
Inmaculada
I
Departamento de Química-Instituto de Tecnología Química UPV-CSIC, Universidad Politécnica de Valencia, Camino de Vera s/n, Apartado 22012, 46071 Valencia, Spain.
Bosca
Francisco
F
Sanchez
Laura
L
Morera
Isabel M
IM
Camps
Pelayo
P
Miranda
Miguel A
MA
D002784:Cholesterol / Q000737:chemistry*; D004951:Esterification; D006859:Hydrogen / Q000737:chemistry*; D008962:Models, Theoretical; D010777:Photochemistry; D013056:Spectrophotometry, Ultraviolet
D006859:Hydrogen; D002784:Cholesterol