Synthesis of 2-Alkyl Chromane-4-ones Using Hydrogen Bond Donor CatalysisPublic
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The total synthesis of biologically active natural product phomoxanthone A has been impeded due to the difficulty in synthesizing its 2-alkyl chromane-4-one core with a stereogenic center. The previous success of silanediol-catalyzed functionalization of benzopyrylium ions with silyl ketene acetals has inspired us to pursue the enantioselective and diastereoselective synthesis of 2-alkyl chroman-4-ones containing two stereocenters using hydrogen bond donor catalysis. The data collected during this study suggests that the influence of hydrogen bond donor catalyst, base, and silyl ketene acetal lead to moderate changes in the diastereomer ratio of the reaction product.
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