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An approach to the synthesis of 5-azaprostacyclin

✍ Scribed by Bernd Radüchel

Publisher
Elsevier Science
Year
1983
Tongue
French
Weight
194 KB
Volume
24
Category
Article
ISSN
0040-4039

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✦ Synopsis

The synthesis of a biologically active 5-azaprostacyclin as well as some of its chemical properties are described. Due to the inherent chemical instability of natural prostacyclin (PGI2) lthere is a great interest in obtaining chemically stable prostacyclin analogs with the same or modified biological profile as PGI2. Several groups have obtained chemically stable PGI2-analogs by replacing the enol ether oxygen in 1 by a sulfur or nitrogen atom2 as well as by a methylene group3. In this paper is described the synthesis of the optically active 5-azaprostacyclin-derivative 3 in which the enol ether system has been replaced by an imino ether moiety. Only a few examples of exocyclic 2-iminotetrahydrofurans have appeared in the literature. These have been usually obtained from&-hydroxy-nitriles or unsaturated nitriles4, from the cyclization of o-halo amides or the condensation of primary amines with 2,2-diethoxytetrahydrofuran5. Attempts to cyclize the nitrile 4" and alkylate the intermediate with ethyl 4-bromobutyrate were not successful.

It therefore became necessary to devis e another approach for the preparation of 5-azaprostacyclin.

2 R=H 3 R=C2H5

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