Some reactions of 16 alpha,17 alpha-oxido-5 alpha-cholestane derivatives, synthesis of 17 alpha-hydroxycholest-4-en-3-one.
Careful epoxidation of the delta 16-olefins 3 and 4 yielded 16 alpha,17 alpha-epoxides 5 and 6 which were reduced by lithium aluminium hydride, oxidized, and dehydrated to 17 alpha-hydroxycholest-4-en-3-one 20, i.e., an epitestosterone homolog containing a well tolerated alkyl group at position 17. Under catalysis of acids, epoxide 5 was rearranged to delta 13-16 alpha-alcohol 10. Less careful epoxidation of delta 16-olefin 4 with excess of peroxy acid led to products of double epoxidation (i.e., epoxidation, rearrangement, and another oxidation) 7 and 12. Structures of products of rearrangement were studied mainly by NMR spectroscopy.
Velgová
H
H
Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, The Czech Republic.
Kasal
A
A
Budĕsínský
M
M
D000475:Alkenes / Q000737:chemistry; D002777:Cholestanols / Q000138:chemical synthesis*; D004845:Epitestosterone / Q000031:analogs & derivatives*; D004852:Epoxy Compounds; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013055:Spectrophotometry, Infrared
D000475:Alkenes; D002777:Cholestanols; D004852:Epoxy Compounds; C089054:17-hydroxycholest-4-en-3-one; D004845:Epitestosterone