%0 Generic
%9 Doctoral Dissertation
%A Chandra, Binita
%D 2010
%F pittir:9681
%K  macrolide synthesis; polypropionates; stereotetrad; AAC; erythronolide B
%T Catalytic Asymmetric Synthesis of Complex Polypropionates:A Synthesis of Erythronolide B
%U http://d-scholarship-dev.library.pitt.edu/9681/
%X Studies towards the total synthesis of the polypropionate macrolide agycone Erythronolide B have been presented. Catalytic asymmetric AAC methodology has been applied to efficiently generate the C10-C13 and the C4-C5 stereocenters in the polypropionate fragments 105 and 209 through â-lactones 76, 80, and 86 respectively. An efficient installation of the C2 and C3-stereocenters in 193 was realized through a Lewis-base catalyzed Mukaiyama aldol reaction. Finally, a highly stereoselective aldol coupling of fragments 105 and 209 was used to join the fragments together.