%A Thomas R. Vargo
%T Catalytic Asymmetric Aldol Equivalents for an Enantioselective Total Synthesis of Apoptolidin C
%X Apoptolidin C is a biologically active polypropionate macrolide isolated from the soil bacteria Nocardiopsis sp.  The work presented herein highlights a novel approach to synthesizing the core of the natural product, apoptolidinone C, as well as a de-novo synthesis of the C9 sacharide.  Our synthesis utilizes a catalytic asymmetric approach to the construction of the complex polypropionate arrays contained in apoptolidin through the use of our acyl halide-aldehyde cyclocondensation (AAC) reaction.  Employing the AAC technology using cinchona alkaloid derived catalysts, as well as the complementary chiral aluminum catalysts, we have successfully demonstrated a catalytic and asymmetric synthesis of the aglycone core of apoptolidin C.   In addition, we have demonstrated the asymmetric synthesis of the C9 saccharide from achiral starting materials.
%D 2012
%K Organic Synthesis Natural Product
%I University of Pittsburgh
%L pittir6166