A de novo enantioselective total synthesis of (-)-laulimalide.
An enantioselective total synthesis of the naturally occurring anticancer agent (-)-laulimalide is described. The synthesis is characterized by extensive use of new reaction methodologies based on catalytic asymmetric acyl halide-aldehyde cyclocondensation (AAC) reactions and transformations of the derived enantioenriched beta-lactones. The synthesis also incorporates a unique allenylstannane glycal acetate alkylation and chemoselective ring-closing metathesis reaction.
Nelson
Scott G
SG
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA. sgnelson@pitt.edu
Cheung
Wing S
WS
Kassick
Andrew J
AJ
Hilfiker
Mark A
MA
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D018942:Macrolides; D017239:Paclitaxel / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism; D043823:Taxoids
D000970:Antineoplastic Agents; D018942:Macrolides; D043823:Taxoids; C117305:laulimalide; D017239:Paclitaxel