Enantioselective synthesis of (−)-cytoxazone and (+)-epi-cytoxazone, novel cytokine modulators via Sharpless asymmetric epoxidation and l-proline catalyzed Mannich reaction |
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| Authors: | Abhimanyu S. Paraskar |
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| Affiliation: | Chemical Engineering and Process Development Division, National Chemical Laboratory, Pashan Road, Pune 411008, Maharashtra, India |
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| Abstract: | A short and efficient enantioselective synthesis of (−)-cytoxazone and its stereoisomer (+)-epi-cytoxazone, novel cytokine modulators, has been described with good yield and enantioselectivity. Ti-catalyzed Sharpless asymmetric epoxidation of allyl alcohol and l-proline catalyzed three-component Mannich reaction constitute the key steps in introducing stereogenicity into the molecule. |
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| Keywords: | Asymmetric synthesis Aminohydroxylation Epoxidation Mannich reaction Oxidation Ozonolysis |
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