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  • 1
    Electronic Resource
    Electronic Resource
    Total synthesis of angucyclines, 7Part 6: Ref.. Hydroaromatic angucyclines of the SF-2315 type (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 1981-1985 
    Details
    ISSN: 0947-3440
    Keywords: Angucyclines ; Diels-Alder reactions ; Photooxygenation ; Methoxylation ; Osmylation ; X-ray ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Osmylation of the Diels-Alder adduct 3 afforded the cis-diol 4, which was dehydrated by acid treatment to the phenol 6. Reaction with tetrafluoroboric acid converted the diol 4 by intramolecular acyl shift into the acetate 7. The relative stereochemistry of 7 was determined by single-crystal X-ray analysis. Photooxygenation of 4 afforded the C-1 carbonyl compound 8 and treatment with sulfuric acid the silanol 9. Functionalization of C-6 was achieved by treatment of 4 with methanolic KOH to yield the cis-methyl ether 11.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1995199511277
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    Paper (German National Licenses)
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  • 2
    Electronic Resource
    Electronic Resource
    Total Synthesis of Angucyclines, 1. - Synthesis of a Daunomycinone-Rabelomycin Hybrid (1993)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1993 (1993), S. 911-913 
    Details
    ISSN: 0170-2041
    Keywords: Rabelomycin ; Angucyclines ; Hydroxylation ; Photooxygenation ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis of the racemic angucyclinone hybrid 3 which combines the structural features of rabelomycin (1) and daunomycinone (2) is described. Key steps are the cyclization of the bromide 6b by a Marshalk-type reaction to yield the angular skeleton 7b, introduction of the tertiary hydroxy group by bromination to 11, solvolysis to 12 and photoinduced oxygenation to afford the C-1 ketone 3.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1993199301143
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    Paper (German National Licenses)
    Fulltext
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