Diastereoselective Synthesis of <Emphasis Type="Italic">cis</Emphasis>-2,6-Disubstituted Perhydro-4-pyranones Using Elevated Pressure Hydrogenation |
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| Authors: | Email author" target="_blank">Marko D?MihovilovicEmail author Helmut?Spreitzer |
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| Institution: | (1) Institute of Applied Synthetic Chemistry, Vienna University of Technology, A-1060 Vienna, Austria (EU);(2) Institute of Pharmaceutical Chemistry, Vienna University, A-1090 Vienna, Austria (EU) |
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| Abstract: | Summary. A diastereoselective strategy for the synthesis of γ-pyrons was developed, starting from the Mg diacetonedicarboxylate complex. Initial cyclization with suitable anhydrides or acid chlorides, followed by hydrolytic decarboxylation leads to 2,6-disubstituted pyrans. Elevated pressure hydrogenation using Pd/C affords the title compounds in high diastereoselectivity. Scope and limitations of the method are outlined on selected examples. |
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| Keywords: | , Reduction, γ,-Pyrons, Magnesium diacetonedicarboxylate complex, Cyclization, |
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