- Synthesis of 5β,17α-19-norpregn-20-yne-3β,17-diol and of 5β,17α-19-norpregn-20-yne-3α,17-diol, human metabolites of norethindrone
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A convenient synthesis of both 5β, 17α-19-norpregn-20-yne-3β,17-diol (1) and 5β,17α-19-norpregn-20-yne-3α, 17-diol (2) in multigram quantities from estr-4-ene-3, 17-dione is reported. Full characterization of these often-cited human melaholites of norethindrone is presented for the first time.
- Curts, Stephen W.,Wren, Douglas L.,Cooper, Gary F.
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- Photoinduced Molecular Transformations. Part 112.Transformation of Steroids into Ring-A-Aromatized Steroids and 19-Norsteroids involving a Regioselective β-Scission of Alkoxyl Radicals; Synthesis of Two Marine Natural Products, 19-Nor-5α-cholestan-3β-ol and 19-norcholest-4-en-3-one...
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A new transformation of steroids into 19-norsteroids and ring-A-aromatized steroids is described.The transformation method involves the removal of the 10β-methyl group by a regioselective β-scission of alkoxyl radicals.Cholesterol was transformed into two marine natural products, 19-nor-5α-cholestan-3β-ol and 19-norcholest-4-en-3-one, and into 19-norcholesta-1,3,5(10)-trien-3-ol.Transformations of 3β-hydroxyandrost-5-en-17-one into 19-nortestosterone, estrone, and the related estranes are also described.
- Suginome, Hiroshi,Senboku, Hisanori,Yamada, Shinji
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p. 2199 - 2205
(2007/10/02)
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- Stereochemistry of the Palladium-catalyzed Hydrogenation of 3-Oxo-4-ene Steroids. V. A Kinetic Study in Basic and Acidic Media
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Effects of the β-methyl group at C-10 and some oxygen functions (=O, OH, OAc) at C-11, C-17, and C-20 on the rates of hydrogenation of 3-oxo-4-ene steroids have been studied with palladium catalyst in pyridine or THF/HBr as solvent.In contrast to the hydrogenation in pyridine, the rate in THF/HBr was greatly depressed by the presence of 10β-methyl group.The reactivity of the steroids was enhanced by the oxygen functions, in particular, by 11, 17-dioxo group.The effects of the substituents are discussed from a mechanistic consideration based on the obtained results.
- Nishimura, Shigeo,Momma, Yasuhiro,Kawamura, Hideo,Shiota, Michio
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p. 780 - 783
(2007/10/02)
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- Microbiological Transformations. XIII. Transformations of 19-Nor and 19-Hydroxy Analogues of Testosterone and Androstendione by Means of Rhodotorula mucilaginosa Strain
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Preparative transformation carried out
- Dmochowska-Gladysz, Jadwiga,Tlomak, Elzbieta,Siewinski, Antoni
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