Synthesis of 2-Alkyl Chromane-4-ones Using Hydrogen Bond Donor Catalysis

Hatt, Jessica Elizabeth

Student Work

Synthesis of 2-Alkyl Chromane-4-ones Using Hydrogen Bond Donor Catalysis

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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.

This report represents the work of one or more WPI undergraduate students submitted to the faculty as evidence of completion of a degree requirement. WPI routinely publishes these reports on its website without editorial or peer review.

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