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  • 1
    Electronic Resource
    Electronic Resource
    Umlagerungen von 1-Methyl-Δ1-3-keto-steroiden zu 1-Methylen-steroiden (1964)
    Springer
    Naturwissenschaften 51 (1964), S. 86-87 
    Details
    ISSN: 1432-1904
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology , Natural Sciences in General
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00635392
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  • 2
    Electronic Resource
    Electronic Resource
    Mikrobiologische Umwandlung von Steroiden, XVII. Darstellung von unterschiedlichen Mono- und Diketostrukturen von D-Homo-4-pregnen-3,20-dion und D-Homo-1,4-pregnadien-3,20-dion (1980)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 113 (1980), S. 203-220 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Microbial Transformations of Steroids, XVII. Preparation of Several Mono- and Diketo-structures of D-Homo-4-pregnene-3,20-dione and D-Homo-1,4-pregnadiene-3,20-dione11α- (2) and 15α-monohydroxy- (3), 6β,11α-(4), 11α,15α- (5), 12β,15α- (6), 15α,16α- (7), 7β,11α- (8), 11β,17α- (9), 7β,17α-dihydroxy- (11), and 17α-hydroxy-11-oxo-D-homoprogesterone (10) were prepared by microbiological transformations of D-homoprogesterone (1) with various fungi. The compounds were oxidized by the method of Jones before and after microbiological 1,2-dehydrogenation with Bacillus lentus to the corresponding keto-structures 12 to 17 and 20 respectively 26 to 30. The 14α-hydroxy-11-ketone 18 and 7α,14α-dihydroxy-11-ketone 19 were obtained by microbiological hydroxylation of the 11-ketone 12 with Curvularia lunata. Penicillium lilacinum degraded D-homoprogesterone (1) to D-homotestosterone.
    Notes: Durch mikrobiologische Umwandlung von D-Homoprogesteron (1) mit verschiedenen Pilzstämmen wurden 11α- (2) und 15α-Monohydroxy- (3), 6β,11α- (4), 11α,15α- (5), 12β,15α- (6), 15α,16α- (7), 7β,11α- (8), 11β,17α- (9), 7β,17α-Dihydroxy- (11) und 17α-Hydroxy-11-oxo-D-homo-progesteron (10) hergestellt. Die Verbindungen wurden vor und nach mikrobiologischer 1,2-Dehydrierung mit Bacillus lentus zu den entsprechenden Ketostrukturen 12 - 17 und 20 bzw. 26 - 30 nach Jones oxidiert. Ein 14α-Hydroxy-11-keton 18 und 7α,14α-Dihydroxy-11-keton 19 wurden durch mikrobiologische Zweithydroxylierung des 11-Ketons 12 mit Curvularia lunata erhalten. Penicillium lilacinum baute D-Homoprogesteron (1) zu D-Homotestosteron ab.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19801130121
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  • 3
    Electronic Resource
    Electronic Resource
    Die Synthese von 16α,18-Dimethylcorticosteroiden (1975)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 108 (1975), S. 54-63 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: The Synthesis of 16α,18-DimethylcorticosteroidsThe syntheses of 16α,18-dimethylcorticoids 5, 7 and 9 starting from 21-acetoxy-6α-fluoro-16α,18-dimethyl-4-pregnen-3,20-dione (1) are described.
    Notes: Die Synthese der 16α,18-Dimethylcorticoide 5, 7 und 9 aus 21-Acetoxy-6α-fluor-16α,18-dimethyl-4-pregnen-3,20-dion (1) wird beschrieben.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19751080108
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  • 4
    Electronic Resource
    Electronic Resource
    1α-Methyl-steroide, II. 1α-Methyl-corticoide (1963)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 96 (1963), S. 2765-2771 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: In der Corticoid-Reihe wurde durch Grignard-1.4-Addition in Δ1.4.6-Trien-3-ketone mit geschützter C-17-Seitenkette die 1α-Methylgruppe eingeführt. 1α-Methyl-cortexolon wurde mikrobiologisch in 11β-Stellung hydroxyliert.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19630961034
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  • 5
    Electronic Resource
    Electronic Resource
    Reaktionen an 16α-Chlormethyl-steroiden (1962)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 95 (1962), S. 2956-2959 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Verbindungen der Pregnan-Reihe vom Typ III erleiden durch Alkali Ringschluß zu Oxetan-Derivaten vom Typ IV.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19620951218
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  • 6
    Electronic Resource
    Electronic Resource
    1.2β-Methylen-steroide (1966)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 99 (1966), S. 1118-1127 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 1.2β-Methylen-3-ketone der Steroidreihe wurden aus Δ1-3β-Hydroxy-Verbindungen durch Methylenierung mit Bis(jodmethyl)-zink-zinkjodid und anschließende Oxydation sowie aus Δ1-3-Keto-AB-cis-steroiden mittels Dimethylmethylensulfoniumoxid und Basen hergestellt. Die 1.2β-Stellung der Methylengruppe wurde durch chemische Reaktionen sichergestellt. Verätherungen, Acetalisierungen, Dehydrierungen, Doppelbindungsisomerisierungen und Reduktionen werden teilweise durch den Cyclopropanring entscheidend beeinflußt.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19660990406
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  • 7
    Electronic Resource
    Electronic Resource
    D-Homosteroide I. Synthese von gestagen-wirksamen D-Homopregnan-DerivatenHerrn Dr. Otto Isler zum 70. Geburtstag gewidmet (1980)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 63 (1980), S. 1867-1890 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis of a series of hormonally active D-homopregnane derivatives is reported.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19800630713
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  • 8
    Electronic Resource
    Electronic Resource
    Über 7-Methyl-steroide (1963)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 96 (1963), S. 2772-2773 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Durch Grignard-1.6-Addition wird aus dem 17.20;20.21-Bis-methylendioxy-Δ1.4.6.9〉(11)-pregnatetraen-on-(3) das 7ζ-Methyl-17.20; 2021 20.21-bis-methylendioxy-Δ1.5.9(11)-pregnatrien-on-(3) erhalten.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19630961035
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  • 9
    Electronic Resource
    Electronic Resource
    Blockierung der mikrobiologischen 11β-Hydroxylierung von Steroiden durch 18-Methyl-Substitution (1969)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 726 (1969), S. 161-167 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Blocking of the Microbiological 11β-Hydroxylation of Steroids by 18-Methyl SubstitutionThe microbiological 11β-hydroxylation of testosterone and Reichstein substance S is sterically blocked by an 18-methyl(13-ethyl) substitution. Instead, well-known side reactions predominate. Thus, hydroxylation of 18-methyltestosterone (1) with Stachylidium theobromae affords mainly 6β-hydroxy-18-methyl-4-androsten-3,17-dione (2); hydroxylation with Curvularia lunata, on the other hand, leads mainly to the 14α-hydroxy derivatives 3 and 4. The latter named fungus converts O(21)-acetyl-18-methyl-Reichstein substance S into the 14α- and 15α-hydroxy compounds 6 and 7.
    Notes: Die mikrobiologische 11β-Hydroxylierung von Testosteron und Reichstein-Substanz S wird durch einen 18-Methyl-Substituenten (13-Äthyl-Gruppe) sterisch blockiert. Stattdessen treten die bekannten Nebenreaktionen dieser Reaktionen in den Vordergrund. So liefert 18-Methyltestosteron (1) bei Hydroxylierung mit Stachylidium theobromae vorwiegend 6β-Hydroxy-18-methyl-4-androsten-3.17-dion (2), mit Curvularia lunata hingegen vor allem die 14α-Hydroxy-Derivate 3 und 4. Der letztgenannte Pilz führt O(21)-Acetyl-18-methyl-Reichstein-Substanz S in die 14α- und 15α-Hydroxy-Verbindungen 6 und 7 über.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.19697260123
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  • 10
    Electronic Resource
    Electronic Resource
    Reaktionen an 18-Methyl-steroiden (1971)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 752 (1971), S. 78-85 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reactions of 18-Methylsteroids1,4-Addition of methylmagnesium iodide to the 18-methyl-Δ16-20-ketones 1 affords by choice 16α-methyl-17α-hydroperoxides 3 or 16α-methyl-20-ketones 4 in 70-80° yield. - The steric course of the addition of bromine/fluorine to Δ5-steroids 6, depends on the reaction conditions. 6 can be transformed either to the 5α-fluoro-6β-bromo compounds 7 or to the isomeric 6β-fluoro-5α-bromo derivatives 9.
    Notes: Durch 1.4-Addition von Methylmagnesiumjodid an 18-Methyl-Δ16-20-ketone 1 lassen sich wahlweise 16α-Methyl-17α-hydroperoxide 3, oder 16α-Methyl-20-ketone 4 in 70-80 proz. Ausbeute herstellen. - Der sterische Verlauf der Brom/Fluor-Anlagerung an Δ5-3β-Hydroxysteroide 6 hängt von den Reaktionsbedingungen ab und kann entweder zu 5α-Fluor-6β-bromsteroiden 7 oder zu 6β-Fluor-5α-brom-steroiden 9 gelenkt werden.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.19717520111
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