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  • 1
    Electronic Resource
    Electronic Resource
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 64 (1981), S. 2251-2256 
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Partial Synthesis of Grandidones A, 7-Epi-A, B, 7-Epi-B, C, D and 7-Epi-D, from 14-HydroxytaxodioneOxydative addition of coleon U (6) to 14-hydroxytaxodione (5) in the presence of Fétizon's reagent mainly leads to grandidone A (1a) and 7-epigrandidone A (1b) (ca. 15:1), whereas coleon V (7) and 5 under the same conditions yield grandidone B (2a) and 7-epigrandidone B (2b) (ca. 3:1). Dimerization of 14-hydroxytaxodione (5) gives grandidone C (3; ca. 40%), grandidone D (4a; ca. 50%) and 7-epigrandidone D (4b; ca. 10%). All these compounds obtained by partial synthesis are in every respect identical with the natural products, thus establishing their absolute configurations. The thermal transformation of grandidone C (3) to grandidone D (4a)/7-epigrandidone D (4b) and interconversions of 4a and 4b were achieved.Oxydative addition of coleon U (6) to 14-hydroxytaxodione (5) in the presence of Fétizon's reagent mainly leads to grandidone A (1a) and 7-epigrandidone A (1b) (ca. 15:1), whereas coleon V (7) and 5 under the same conditions yield grandidone B (2a) and 7-epigrandidone B (2b) (ca. 3:1). Dimerization of 14-hydroxytaxodione (5) gives grandidone C (3; ca. 40%), grandidone D (4a; ca. 50%) and 7-epigrandidone D (4b; ca. 10%). All these compounds obtained by partial synthesis are in every respect identical with the natural products, thus establishing their absolute configurations. The thermal transformation of grandidone C (3) to grandidone D (4a)/7-epigrandidone D (4b) and interconversions of 4a and 4b were achieved.Oxydative addition of coleon U (6) to 14-hydroxytaxodione (5) in the presence of Fétizon's reagent mainly leads to grandidone A (1a) and 7-epigrandidone A (1b) (ca. 15:1), whereas coleon V (7) and 5 under the same conditions yield grandidone B (2a) and 7-epigrandidone B (2b) (ca. 3:1). Dimerization of 14-hydroxytaxodione (5) gives grandidone C (3; ca. 40%), grandidone D (4a; ca. 50%) and 7-epigrandidone D (4b; ca. 10%). All these compounds obtained by partial synthesis are in every respect identical with the natural products, thus establishing their absolute configurations. The thermal transformation of grandidone C (3) to grandidone D (4a)/7-epigrandidone D (4b) and interconversions of 4a and 4b were achieved.Oxydative addition of coleon U (6) to 14-hydroxytaxodione (5) in the presence of Fétizon's reagent mainly leads to grandidone A (1a) and 7-epigrandidone A (1b) (ca. 15:1), whereas coleon V (7) and 5 under the same conditions yield grandidone B (2a) and 7-epigrandidone B (2b) (ca. 3:1). Dimerization of 14-hydroxytaxodione (5) gives grandidone C (3; ca. 40%), grandidone D (4a; ca. 50%) and 7-epigrandidone D (4b; ca. 10%). All these compounds obtained by partial synthesis are in every respect identical with the natural products, thus establishing their absolute configurations. The thermal transformation of grandidone C (3) to grandidone D (4a)/7-epigrandidone D (4b) and interconversions of 4a and 4b were achieved.
    Type of Medium: Electronic Resource
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