Short and efficient total synthesis of fraxinellone limonoids using the stereoselective Oshima-Utimoto reaction.
[reaction: see text] The catalytic diastereoselective Oshima-Utimoto reaction was employed for the construction of fraxinellone and related members of this limonoid family of natural products. After formation of the five-membered lactone, a stereoselective aldol reaction and olefin metathesis established the bicyclic ring system in the natural products.
Trudeau
Stéphane
S
Department of Chemistry, The University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.
Morken
James P
JP
D001572:Benzofurans / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D036701:Limonins / Q000138:chemical synthesis*; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
D001572:Benzofurans; D036701:Limonins; C075391:fraxinellone