Asymmetric synthesis of (-)-dihydroxanthatin by the stereoselective Oshima-Utimoto reaction.
[reaction: see text]. The catalytic stereoselective Oshima-Utimoto reaction is useful for the construction of five-membered oxacycles from simple starting materials and was employed for the preparation of the lactone group in the asymmetric synthesis of (-)-11alpha,13-dihydroxanthatin. Completion of the synthesis is facilitated by ring-closing enyne metathesis and alkene cross metathesis reactions.
Evans
Michael A
MA
Department of Chemistry, The University of North Carolina at Chapel Hill, 27599-3290, USA.
Morken
James P
JP
D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
C510341:11,13-dihydroxanthatin; D005663:Furans