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  • 1
    Electronic Resource
    Electronic Resource
    Asymmetrische Totalsynthese von 19-Nor-Steroiden mit photochemischer Schlüsselreaktion: Enantiomerenreine Zielverbindungen (1982)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1982 (1982), S. 1999-2040 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Asymmetric Total Synthesis of 19-Nor-Steroids via a Photochemical Key Reaction: Enantiomerically Pure Target CompoundsA total synthesis of the enantiomerically pure 19-nor-steroids estrone (1a), 19-norandrost-4-en-3,17-dione (2a), estradiol-17β (3a), and 19-nortestosterone (4a) is described. It follows the A + D→AD→ABCD sequence, proceeds via a kinetically unstable o-quinodimethane derivative obtained in a light induced reaction, and employs the chiral synthetic building block dimethyl (R)-2-vinyl-1,1-cyclopropanedicarboxylate (12b). The latter is easily accessible by an asymmetry inducing ScN′ reaction. During the synthetic procedure it is isolated enantiomerically pure. The analytic procedure reveals that 12b is formed with an optical purity or an enantiomeric excess, respectively, of 95%.
    Notes: Eine Totalsynthese der enantiomerenreinen 19-Nor-Steroide Östron (1a), 19-Norandrost-4-en-3,17-dion (2a), östradiol-17β (3a) und 19-Nortestosteron (4a) wird beschrieben. Sie folgt dem A + D→AD→ABCD-Aufbauprinzip, durchläuft ein lichtinduziertes, kinetisch instabiles o-Chinodimethan-Derivat und verwendet den chiralen Synthesebaustein (R)-2-Vinyl-1,1-cyclopropan-dicarbonsäure-dimethylester (12b). 12b ist durch eine Asymmetrie induzierende ScN′-Reaktion (s. Abb. 2) bequem zugänglich. Bei der Synthese fällt 12b enantiomerenrein an. Das analytische Procedere offenbart, daß 12b mit einer optischen Reinheit oder mit einem Enantiomeren-überschuß jeweils von 95% zustande kommt.
    Additional Material: 8 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198219821109
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  • 2
    Electronic Resource
    Electronic Resource
    Novel Rearrangement of 1,2:4,8-Diepoxy-p-menthane (1983)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1983 (1983), S. 1446-1447 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Neue Umlagerung von 1,2:4,8-Diepoxy-p-menthanErhitzen von 1,2:4,8-Diepoxy-p-methan (1) mit Aluminiumoxid in Toluol induziert eine Fragmentierung zum 6-Ethenyl-5,6-dihydro-2,2,6-trimethyl-2H-pyran-3(4H)-on (2).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198319830817
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  • 3
    Electronic Resource
    Electronic Resource
    Hochselektive Totalsynthese von 19-Nor-Steroiden mit photochemischer Schlüsselreaktion: Racemische Zielverbindungen1,4) (1981)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1981 (1981), S. 2335-2371 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Highly Selective Total Synthesis of 19-Nor-Steroids via a Photochemical Key Reaction: Racemic Target Compounds1,4)Ring A and ring D building blocks 17b and rac-15, easily available from m-cresyl methyl ether (19a) or (E)-1,4-dibromo-2-butene (13b) and methyl malonate (14a), respectively, react by Michael addition affording the key compound rac-9a. The latter compound by successive photoenolization, intramolecular Diels/Alder reaction, and dehydration furnishes the pretarget compounds rac-5 and rac-6. From here the 19-norsteroids rac-estrone (rac-1a), rac-19-norandrost-4-ene-3,17-dione (rac-2a), rac-estradiol-17β (rac-3a), and rac-19-nortestosterone (rac-4a) are optionally accessible (cf. schemes 1 and 2 as well as tables 3 and 4).
    Notes: Die Ring A- und Ring D-Bausteine 17b und rac-15, die bequem aus m-Kresolmethylether (19a) sowie (E)-1,4-Dibrom-2-buten (13b) und Malonsäure-dimethylester (14a) zugänglich sind, fügen sich in einer Michael-Addition zur Schlüsselverbindung rac-9a zusammen. Letztere reagiert nacheinander durch Photoenolisierung, intramolekulare Diels/Alder-Reaktion und Dehydratisierung zu den Präzielverbindungen rac-5 und rac-6. Von hier aus erhält man wahlweise die 19-Nor-Steroide rac-Östron (ra-1a), rac-19-Norandrost-4-en-3,17-dion (rac-2a), rac-Östradiol-17β (rac-3a) und rac-19-Nortestosteron (rac-4a) (s. Schemata 1 und 2 sowie Tab. 3 und 4).
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198119811220
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