ol9b03379_si_001.pdf (3.06 MB)
En Route to D‑Ring Inverted Phorbol Esters
journal contribution
posted on 2019-10-18, 18:34 authored by Sharon Chow, Tanja Krainz, Paul V. Bernhardt, Craig M. WilliamsPhorbol 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.