A common approach to the total synthesis of l-arabino-, l-ribo-C18-phytosphingosines, ent-2-epi-jaspine B and 3-epi-jaspine B from d-mannose |
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Authors: | Miroslava Martinková Kvetoslava PomikalováJozef Gonda Mária Vilková |
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Institution: | Institute of Chemical Sciences, Department of Organic Chemistry, P. J. Šafárik University, Moyzesova 11, Sk-040 01 Košice, Slovak Republic |
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Abstract: | A common strategy for the total syntheses of the protected l-arabino- and l-ribo-C18-phytosphingosine (8 and 9, respectively), HCl salts of ent-2-epi-jaspine B (ent-6) and 3-epi-jaspine B (7) with efficient use of both flexible building blocks 26 and 27 was achieved. The key step of this approach was 3,3]-sigmatropic rearrangement of allylic trichloroacetimidate 21 and thiocyanate 22, which were derived from the known 2,3:5,6-di-O-isopropylidene-d-mannofuranose 18 as the source of chirality. The side chain functionality was installed utilizing a Wittig reaction. |
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Keywords: | Sphingolipids Phytosphingosine Jaspine B Rearrangements Trichloroacetamides Isothiocyanates |
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