Synthesis and 13C-NMR analysis of 5 alpha- and 5 beta-cholestane-3,6-dione.
Starting from cholesterol a simple and efficient synthesis of 5 alpha-cholestane-3,6-dione and 5 beta-cholestane-3,6-dione is described. The 13C shielding data of C-7, C-9, and C-19 in both isomers can be used in the determination of the stereochemistry at C-5 of these compounds. The combination of 13C NMR spectroscopy and the simple synthesis of both isomers offers good opportunities for the determination of the stereochemistry at C-5 of 3,6-dioxosteroids.
Wijnberg
J B
JB
Laboratory of Organic Chemistry, Agricultural University, Wageningen, The Netherlands.
de Groot
A
A
D002778:Cholestanones / Q000032:analysis; D002783:Cholestenones; D002784:Cholesterol; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism
D002778:Cholestanones; D002783:Cholestenones; C061920:cholestane-3,6-dione; C000475:cholest-4-en-3-one; D002784:Cholesterol