Some reactions of 16α,17α-oxido-5α-cholestane derivatives, synthesis of 17α-hydroxycholest-4-en-3-one
1994; Elsevier BV; Volume: 59; Issue: 5 Linguagem: Inglês
10.1016/0039-128x(94)90123-6
ISSN1878-5867
AutoresH. VELGOVA, Alexander Kasal, Milos̆ Budĕs̆ı́nský,
Tópico(s)Plant biochemistry and biosynthesis
ResumoCareful 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.
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