%A Joseph Burchick
%T Functional Group Transposition of Bicyclo[5.3.0]decadienones Afforded by the Allenic Pauson-Khand Reaction. An Approach Toward the Total Synthesis of (?)-Dehydroleucodine
%X The allenic Pauson-Khand reaction (APKR) has proven to be a powerful method for the
construction of seven-membered rings. Despite this, only a few reports of this methodology being
employed in total syntheses exist. Reported herein are synthetic studies targeted towards the
elaboration of APKR adducts via the functionalization of the resulting enone motif. In addition, a
rapid synthetic route towards the core 5,7,5-framework of biologically active 6,12-guaianolides
was developed in an enantioselective fashion, utilizing the APKR as they key ring-forming step.
The successful APKR adduct functionalization studies were combined with this novel synthetic
route in an effort towards the first total synthesis of (?)-dehydroleucodine.
%D 2021
%K allenic pauson-khand reaction, catalysis, total synthesis
%I University of Pittsburgh
%L pittir40005