1778-02-5Relevant articles and documents
Oxygen-functionalization of C13-angular methyl group in pregnane steroid by means of intramolecular carbony-mediated anodic oxidation
Shibuya,Murakami,Shimada,Yoshikawa,Kitagawa
, p. 1143 - 1147 (1992)
An oxygen-functionalization of the C13-angular methyl group in 3β-acetoxy-5α-pregnan-20-one and its tetra-O-acetyl-β-D-glucopyranosyl derivative has been effected by means of an anodic oxidation mediated by the C20-carbonyl residue in the steroid skeleton.
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Heyl,Herr,Centolella
, p. 247 (1949)
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Ammonium formate/palladium on carbon: A versatile system for catalytic hydrogen transfer reductions of carbon-carbon double bonds
Paryzek, Zdzislaw,Koenig, Hanna,Tabaczka, Bartlomiej
, p. 2023 - 2026 (2003)
Various carbon-carbon double bonds in olefins and α,β -unsaturated ketones were effectively reduced to the corresponding alkanes and saturated ketones, using ammonium formate as a hydrogen transfer agent in the presence of Pd/C as catalyst in refluxing methanol.
A Mild and Efficient Method for the Reduction of Oximes to Imines for Further in situ Reactions
Barton, Derek H. R.,Motherwell, William B.,Simon, Ethan S.,Zard, Samir Z.
, p. 337 - 338 (1984)
Tributylphosphine-diphenyl disulphide is an effective and mild reagent for reducing oximes to imines.
Convenient synthesis of new pregnenolone oximinyl oxalate dimers
Nahar,Sarker,Turner
, p. 315 - 318 (2008)
Three new symmetrical pregnenolone oxyminyl oxalate dimers (8-10) were synthesized from the corresponding pregnenolone oximes (3, 5, and 7) at room temperature. All dimers were characterised by spectroscopic means, notably HRFABMS and comprehensive NMR spectroscopic data analyses.
Chaudhuri,Gut
, p. 3737,3743 (1965)
Chemical synthesis of 7α-hydroxypregnenolone, a neuroactive steroid that stimulates locomotor activity
Yoshimoto, Francis K.,Arman, Hadi D.,Griffith, Wendell P.,Yan, Fangzhi,Wherritt, Daniel J.
, p. 50 - 57 (2017)
7α-Hydroxypregnenolone is an endogenous neuroactive steroid that stimulates locomotor activity. A synthesis of 7α-hydroxypregnenolone from pregnenolone, which takes advantage of an orthogonal protecting group strategy, is described. In detail, the C7-position was oxidized with CrO3 and 3,5-dimethylpyrazole to yield a 7-keto steroid intermediate. The resulting 7-ketone was stereoselectively reduced to the 7α-hydroxy group with lithium tri-sec-butylborohydride. In contrast, reduction of the same 7-ketone intermediate with NaBH4 resulted in primarily the 7β-hydroxy epimer. Furthermore, in an alternative route to the target compound, the 7α-hydroxy group was successfully incorporated by direct C–H allylic benzoyloxylation of pregnenolone-3-acetate with CuBr and tert-butyl peroxybenzoate followed by saponification. The disclosed syntheses to 7-oxygenated steroids are amenable to potentially obtain other biologically active sterols and steroids.
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Marker et al.
, p. 1276,1278 (1942)
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TRANSFORMED STEROIDS. 113. CYCLOBUTENOPREGNANES IN CYCLOADDITION AND OXIDATION REACTIONS
Kamernitskii, A. V.,Ignatov, V. N.,Levina, I. S.,El'yanov, B. S.
, p. 1375 - 1377 (1980)
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REACTION OF SOME TRISUBSTITUTED STEROID EPOXIDES WITH TRIPHENYLPHOSPHINE - IODINE DOMPLEX. DEOXYGENATION OF EPOXIDES
Paryzek, Zdzislaw,Wydra, Roman
, p. 2601 - 2604 (1984)
Triphenylphosphine - iodine complex was found to be an effective reagent for deoxygenation of trisubstituted steroidal epoxides.The mechanism of the reaction is proposed.
Uvarova et al.
, p. 79,85 (1973)
SYNTHESIS OF 19-HYDROXYSTEROIDS II. NEW SYNTHESIS OF 19-HYDROXYPROGESTERONE
Kovganko, N. V.,Kashkan, Zh. N.,Chernov, Yu. G.
, p. 589 - 592 (1992)
19-Hydroxyprogesterone has been synthesized in seven stages from pregnenolone with an overall yield of 11percent.
An Intramolecular Iodine-Catalyzed C(sp3)?H Oxidation as a Versatile Tool for the Synthesis of Tetrahydrofurans
Br?se, Stefan,Koch, Vanessa
supporting information, p. 3478 - 3483 (2021/07/22)
The formation of ubiquitous occurring tetrahydrofuran patterns has been extensively investigated in the 1960s as it was one of the first examples of a non-directed remote C?H activation. These approaches suffer from the use of toxic transition metals in overstoichiometric amounts. An attractive metal-free solution for transforming carbon-hydrogen bonds into carbon-oxygen bonds lies in applying economically and ecologically favorable iodine reagents. The presented method involves an intertwined catalytic cycle of a radical chain reaction and an iodine(I/III) redox couple by selectively activating a remote C(sp3)?H bond under visible-light irradiation. The reaction proceeds under mild reaction conditions, is operationally simple and tolerates many functional groups giving fast and easy access to different substituted tetrahydrofurans.
Steroid compound as well as preparation method and application thereof (by machine translation)
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Paragraph 0058-0059; 0060-0061, (2020/10/29)
The compounds have the structure shown in the general formula (I) or the general formula (II); and experiments prove that the compounds can treat three-negative breast cancer by promoting apoptosis. (by machine translation)
