Bismuth(III) triflate-catalyzed direct conversion of corticosteroids into highly functionalized 17-ketosteroids by cleavage of the C17-dihydroxyacetone side chain.
The use of bismuth(III) triflate as catalyst for the direct conversion of corticosteroids into highly functionalized 17-ketosteroids by cleavage of the C17-dihydroxyacetone side chain is reported. This catalytic process is very chemoselective, since functionalities of the starting corticosteroids, such as Delta(4)-3-keto, Delta(1,4)-3-keto, 11beta-hydroxyl, and 9beta,11beta-epoxide, remained intact.
Pinto
Rui M A
RM
Laboratório de Química Farmacêutica, Faculdade de Farmácia, Universidade de Coimbra, 3000-548, Coimbra, Portugal.
Salvador
Jorge A R
JA
Le Roux
Christophe
C
Paixão
José A
JA
D015068:17-Ketosteroids / Q000737:chemistry*; D000096:Acetone / Q000737:chemistry*; D000305:Adrenal Cortex Hormones / Q000737:chemistry*; D002384:Catalysis; D002855:Chromatography, Thin Layer; D009682:Magnetic Resonance Spectroscopy; D008698:Mesylates / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
D015068:17-Ketosteroids; D000305:Adrenal Cortex Hormones; D008698:Mesylates; D000096:Acetone; C445789:Bi(OTf)3