title: Enantioselective total synthesis of borrelidin.
abstract: The first total synthesis of the natural product borrelidin is described. The propionate fragment of the molecule was concisely synthesized through catalytic enantioselective reductive aldol reactions, a catalytic Negishi coupling, and a catalytic directed hydrogenation. The propionate segment was then fused to the vinyl iodide fragment through a catalytic Sonogashira coupling. Subsequent catalytic hydrostannylation and catalytic cyanation allowed access to the target structure.
authors.affiliation: Department of Chemistry, Venable and Kenan Laboratories, The University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.
authors.forename: Matthew O
authors.initials: MO
authors.lastname: Duffey
authors.forename: Arnaud
authors.initials: A
authors.lastname: LeTiran
authors.forename: James P
authors.initials: JP
authors.lastname: Morken
mesh_terms: D020533:Angiogenesis Inhibitors / Q000138:chemical synthesis; D004791:Enzyme Inhibitors / Q000138:chemical synthesis; D005233:Fatty Alcohols / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
chemical_list: D020533:Angiogenesis Inhibitors; D004791:Enzyme Inhibitors; D005233:Fatty Alcohols; C005066:borrelidin