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En Route to D-Ring Inverted Phorbol Esters
Sharon Chow1, Tanja Krainz1, Paul V Bernhardt1
1School of Chemistry and Molecular Biosciences , University of Queensland , Brisbane , 4072 , Australia.
Abstract:
Phorbol esters are long regarded as tumor promotors, due to protein kinase C (PKC) activation, but more recently higher oxidized natural derivatives have been shown to display antitumor activity. Given the synthetic difficulty, systematic non-natural systems are not readily available to further interrogate PKC binding. Herein reported is the concise construction of a considerably advanced intermediate toward D-ring inverted phorbol esters, enabled by a rhodium-catalyzed [4 + 3] cycloaddition involving a highly functionalized tetrahydrobenzofuran.
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