Stereoselective synthesis of pachastrissamine (jaspine B) |
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Authors: | Celia Ribes Miguel Carda |
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Institution: | a Depart. de Q. Inorgánica y Orgánica, Univ. Jaume I, Castellón, E-12080 Castellón, Spain b Depart. de Q. Orgánica, Univ. de Valencia, E-46100 Burjassot, Valencia, Spain |
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Abstract: | A stereoselective synthesis in enantiopure form of the natural anhydrophytosphingosine pachastrissamine (jaspine B), a metabolite isolated from sponges, is described. The chiral epoxide (R)-glycidol was the starting material. Key steps of this synthesis are a Sharpless asymmetric epoxidation, an intramolecular stereospecific epoxide opening mediated by a trichloroacetimidate group, and the formation of a tetrahydrofuran ring via intramolecular nucleophilic displacement. |
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Keywords: | Pachastrissamine (jaspine B) (R)-Glycidol Sharpless asymmetric epoxidation Imidate epoxide opening |
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