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Synthesis of β-Amino Diaryldienones Using the Mannich Reaction
N G R Dayan Elshan1, Matthew B Rettig2,3, Michael E Jung1
1Department of Chemistry and Biochemistry , University of California , Los Angeles , California 90095 , United States.
Abstract:
The Mannich reaction has been used for decades to prepare many pharmaceutically important molecules. Here, using a "double-Mannich-β-elimination" synthetic sequence, we report the synthesis and the characterization details of a novel class of β-amino diaryldienones with prominent antiprostate cancer activity. Through these studies, we correct an erroneous structure in the current literature, present a discussion of the stereochemical outcome of a new reaction, and probe the mechanism(s) of byproduct formation through isotopic studies.
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