The fusicoccane diterpenes have amassed interest for their intricate 5-8-5 tricyclic framework and ability to interface with diverse signaling proteins. Herein, we report an enantioselective synthetic platform for the rapid assembly of fusicoccanes where the 5-8-5 motif is prepared via valence bond isomerization of a polyene precursor. A series of regio- and stereoselective modifications to the periphery of this substructure provides entry to diverse fusicoccane congeners. The utility of this strategy is demonstrated with a concise total synthesis of (+)-fusicoccadiene.
Related links
Details
Title
Enantioselective Total Synthesis of (+)-Fusicoccadiene via Photocatalytic Polyene Isomerization
Publication Details
Journal of the American Chemical Society, Vol.148(1), pp.124-129
Resource Type
Journal article
Publisher
American Chemical Society
Number of pages
6
Grant note
NA / W. Herz Endowment
R01-GM125926 / National Institutes of Health (NIH); United States Department of Health & Human Services; National Institutes of Health (NIH) - USA