Total synthesis of leucascandrolide a: a new application of the Mukaiyama aldol-Prins reaction.
A total synthesis of the marine natural product leucascandrolide A has been completed. The titanium tetrabromide-mediated Mukaiyama aldol-Prins (MAP) reaction with aldehydes developed in our group provided a highly convergent and stereoselective method for assembling the core of the molecule. A new class of MAP reactions with acetals is introduced, and mechanistic considerations for both MAP methods are described. The total synthesis was completed by coupling of the side chain through two avenues: a known Still-Gennari olefination and a new Z-selective aldol/dehydroselenation reaction. Both procedures were highly selective and provided the natural product.
Van Orden
Lori J
LJ
Department of Chemistry, 1102 Natural Sciences II, University of California-Irvine, Irvine, CA 92697, USA.
Patterson
Brian D
BD
Rychnovsky
Scott D
SD
D009682:Magnetic Resonance Spectroscopy; D010080:Oxazoles / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization
D010080:Oxazoles; D012717:Sesquiterpenes; C408748:leucascandrolide A