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Synthons for syntheses of spiro[2.4]heptane analogues of prostaglandins

Ausgangsverbindungen für die Synthese von Prostaglandin-analogen Spiro[2.4]heptanen

  • Organische Chemie Und Biochemie
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Abstract

Methods for the preparation of synthons for syntheses of spiro[2.4]heptane analogues of prostaglandins are described. Two of them (1a and1b) enable the syntheses of 11-deoxy-type compounds and were prepared from spiro[2.4]heptan-4-one (3) which after transformation into the 5-phenylthio-α,β-unsaturated ketone5 was subjected to conjugate addition of organocuprate reagent6. The third synthon (2)-a potential intermediate in syntheses of complete spiro[2.4]heptane analogues of prostaglandins-was prepared from the bicyclic ketone10 byBaeyer-Villiger oxidation followed by epoxidation.

Zusammenfassung

Es werden Synthesewege für Spiro[2.4]hepane als Analoge zu Prostaglandinen beschrieben. Zwei davon (1a und1b) ermöglichen die Synthese von Verbindungen des 11-Deoxy-Typs; sie wurden aus Spiro[2.4]heptan-4-on (3) dargestellt, das nach der Umwandlung zum 5-phenylthio-α,β-ungesättigten Keton5 einer konjugierten Addition von Organocuprat-Reagens6 unterworfen wurde. Das dritte (2), ein potentielles Zwischenprodukt in der Synthese von vollständigen Spiro[2.4]heptan-Analogen zu Prostaglandinen, wurde aus dem bicyclischen Keton10 durchBaeyer-Villiger-Oxidation gefolgt von einer Epoxidierung dargestellt.

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Authors and Affiliations

  1. Department of Chemistry, Technical University (Politechnika), PL-00-662, Warsaw, Poland

    Krzysztof Jarowicki & Tadeusz Jaworski

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  1. Krzysztof Jarowicki
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  2. Tadeusz Jaworski
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Jarowicki, K., Jaworski, T. Synthons for syntheses of spiro[2.4]heptane analogues of prostaglandins. Monatsh Chem 115, 605–612 (1984). https://doi.org/10.1007/BF00799169

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  • DOI: https://doi.org/10.1007/BF00799169

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