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  A Carbohydrate Approach to Polyol Fragments of Amphotericin and the Trienomycin- and Mycotrienin Antibiotics

Fürstner, A., & Baumgartner, J. (1993). A Carbohydrate Approach to Polyol Fragments of Amphotericin and the Trienomycin- and Mycotrienin Antibiotics. Tetrahedron, 49(38), 8541-8560. doi:10.1016/S0040-4020(01)96261-1.

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 Urheber:
Fürstner, Alois1, Autor           
Baumgartner, Judith1, Autor
Affiliations:
1Institute of Organic Chemistry, Technical University, Stremayrgasse 16, A-8010 Graz, Austria, ou_persistent22              

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 Zusammenfassung: Hydrolytically labile ω-chloro-ω-phenyhhioglycosides. obtained from the corresponding ω-phenylthioglycosides on treatment with NCS in CCL4 are readily dealkoxyhalogenated with Zn/Ag-graphite in anhydrous solvents affording enantiomerically pure synthons bearing an aldehyde function at the one end and a vinylthioether group at the other end of the ring-opened product. This fragmentation technique turned out to be general and was used for the synthesis of a building block exhibiting the substitution pattern of the C9-C14 segment common to all trienomycin-, mycotrienin- and ansattienin macrolide antibiotics. Zn/Ag-graphite was also used to reductively ring-open the 6-deoxy-6-iodopyranoside 37, easily accessible from D-glucose, to enal 38. which served as central precursor for the synthesis of both the C1-C6 as well as C7-C13 unit of the polyhydroxylated chain of amphoteronolide B. Combining these two segments 45 and 51 by ketophosphonatelaldehyde coupling afforded enone 54 which is synthetically equivalent to an intermediate of a former total synthesis of this macrolide. Thus, a convergent synthesis of the C1-C13 fragment of amphotericin B based upon the hidden C2-symmetry of this target molecule was achieved using metal-graphite promoted ring-opening of carbohydrates in the key step in combination with formal inversion of the configuration of the resulting hex-5-enals.

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Sprache(n): eng - English
 Datum: 1993-06-031993-07-222001-03-201993-09-17
 Publikationsstatus: Erschienen
 Seiten: 20
 Ort, Verlag, Ausgabe: -
 Inhaltsverzeichnis: -
 Art der Begutachtung: Expertenbegutachtung
 Identifikatoren: DOI: 10.1016/S0040-4020(01)96261-1
 Art des Abschluß: -

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Titel: Tetrahedron
  Andere : Tetrahedron
Genre der Quelle: Zeitschrift
 Urheber:
Affiliations:
Ort, Verlag, Ausgabe: Oxford : Pergamon
Seiten: 20 Band / Heft: 49 (38) Artikelnummer: - Start- / Endseite: 8541 - 8560 Identifikator: ISSN: 0040-4020
CoNE: https://pure.mpg.de/cone/journals/resource/954925448773