Synthesis of 15β-hydroxy-24-oxocholesterol and 15β,29-dihydroxy-7-oxofucosterol

Autor:	Dashan Liu, Trevor C. McMorris, Louise M. Stuhmiller
Rok vydání:	1988
Předmět:	chemistry.chemical_classification Potassium carbonate chemistry.chemical_compound Ketone chemistry Bromide Yield (chemistry) Acetal Organic chemistry Formate Triol Nitrite Medicinal chemistry
Zdroj:	J. Chem. Soc., Perkin Trans. 1. :2161-2167
ISSN:	1364-5463 0300-922X
DOI:	10.1039/p19880002161
Popis:	3β-Acetoxyandrost-5-en-17-one has been converted into 15β-hydroxy-24-oxocholesterol. Reaction of (17E)-3β-(dimethyl-t-butylsilyloxy)-15β,16β-epoxypregna-5,17(20)-diene with the magnesium cyanocuprate derivative of 3-(1,3-dioxolan-2-yl)-4-methylpentyl bromide gave (20R)-3β-(dimethylt-butylsilyloxy)-15β-hydroxy-24-oxocholesta-5,16-diene 24-ethylene acetal in 80% yield, and this was converted into the target compound in high yield by catalytic hydrogenation followed by removal of the protecting groups. Reaction of 3β,15β-diacetoxycholest-5-en-24-one with the anion of diethyl cyanomethylphosphonate and reduction of the resulting nitrite with DIBAL-H, gave 15β,29-dihydroxyfucosterol. This was converted into the 3,29-diacetate 15-formate and oxidized with chromium trioxide–3,5-dimethylpyrazole. Removal of the acetate and formate groups with aqueous potassium carbonate afforded 15β,29-dihydroxy-7-oxofucosterol.
Databáze:	OpenAIRE
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