title: The antibody catalysis route to the total synthesis of epothilones.
abstract: An efficient monoclonal aldolase antibody that proceeds by an enamine mechanism was generated by reactive immunization. Here, this catalyst has been used in the total synthesis of epothilones A (1) and C (3). The starting materials for the synthesis of these molecules have been obtained by using antibody-catalyzed aldol and retro-aldol reactions. These precursors were then converted to epothilones A (1) and C (3) to complete the total synthesis.
authors.affiliation: The Skaggs Institute for Chemical Biology and the Department of Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA. subhash@scripps.edu or ral@scripps.edu
authors.forename: S C
authors.initials: SC
authors.lastname: Sinha
authors.forename: C F
authors.initials: CF
authors.lastname: Barbas
authors.forename: R A
authors.initials: RA
authors.lastname: Lerner
mesh_terms: D017151:Antibodies, Catalytic / Q000737:chemistry* / Q000276:immunology; D034261:Epothilones; D004852:Epoxy Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D005634:Fructose-Bisphosphate Aldolase / Q000737:chemistry / Q000276:immunology*; D013844:Thiazoles / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D017151:Antibodies, Catalytic; D034261:Epothilones; D004852:Epoxy Compounds; D013844:Thiazoles; C093787:epothilone A; D005634:Fructose-Bisphosphate Aldolase