1.
Steroids
; 59(5): 335-40, 1994 May.
Artigo
em Inglês
| MEDLINE
| ID: mdl-8073447
RESUMO
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.
Assuntos
Colestanóis/síntese química , Epitestosterona/análogos & derivados , Alcenos/química , Compostos de Epóxi , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Oxirredução , Espectrofotometria Infravermelho
2.
J Steroid Biochem
; 13(4): 455-60, 1980 Apr.
Artigo
em Inglês
| MEDLINE
| ID: mdl-7190203