Jones oxidation of 5α-cholesta-8,14-dien-3β-yl acetate furnishes 9α-hydroxy-15-oxo-5α-cholest-8(14)-en-3β-yl acetate (4a). Treatment of (4a) with zinc dust and sulphuric acid followed by saponification gives 3β-hydroxy-5α-cholest-8(14)-en-15-one. On the basis of chemical and spectroscopic evidence, the product obtained by oxidation of 5α-cholest-8,14-dien-3β-ol is formulated as 9α-hydroxy- 5α-cholest-8(14)-ene-3,15-dione (4b) and not as 14α-hydroxy- 5α-cholest-8-ene-3,7-dione (3) as reported by others.
A novel synthesis of 3β-hydroxy-5α-cholest-8(14)-en-15-one / M. Anastasia, A. Fiecchi, A. Scala. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - 1979(1979), pp. 1821-1824. [10.1039/P19790001821]
A novel synthesis of 3β-hydroxy-5α-cholest-8(14)-en-15-one
M. AnastasiaPrimo
;
1979
Abstract
Jones oxidation of 5α-cholesta-8,14-dien-3β-yl acetate furnishes 9α-hydroxy-15-oxo-5α-cholest-8(14)-en-3β-yl acetate (4a). Treatment of (4a) with zinc dust and sulphuric acid followed by saponification gives 3β-hydroxy-5α-cholest-8(14)-en-15-one. On the basis of chemical and spectroscopic evidence, the product obtained by oxidation of 5α-cholest-8,14-dien-3β-ol is formulated as 9α-hydroxy- 5α-cholest-8(14)-ene-3,15-dione (4b) and not as 14α-hydroxy- 5α-cholest-8-ene-3,7-dione (3) as reported by others.
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