title: Studies toward the enantiospecific total synthesis of rhodexin A.
abstract: Studies toward the enantiospecific total synthesis of rhodexin A via a very hindered inverse electron demand Diels-Alder reaction are described. The C8-diastereomer of the fully elaborated tetracyclic core of rhodexin A, 23, was prepared in good yield and excellent selectivity using as the key step the stepwise Diels-Alder reaction of the very hindered dienone 3 and the silyl enol ether 4 catalyzed by the very strong Lewis acid, dimethylaluminum triflimide.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA. jung@chem.ucla.edu
authors.forename: Michael E
authors.initials: ME
authors.lastname: Jung
authors.forename: Mikhail
authors.initials: M
authors.lastname: Guzaev
mesh_terms: D018360:Crystallography, X-Ray; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D006027:Glycosides; D007783:Lactones; C482684:rhodexin A