Enantioselective total synthesis of borrelidin.
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.
Duffey
Matthew O
MO
Department of Chemistry, Venable and Kenan Laboratories, The University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.
LeTiran
Arnaud
A
Morken
James P
JP
D020533:Angiogenesis Inhibitors / Q000138:chemical synthesis; D004791:Enzyme Inhibitors / Q000138:chemical synthesis; D005233:Fatty Alcohols / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
D020533:Angiogenesis Inhibitors; D004791:Enzyme Inhibitors; D005233:Fatty Alcohols; C005066:borrelidin