title: First total synthesis of rhodexin A.
abstract: An efficient total synthesis of rhodexin A (1) is reported. An initial inverse-electron-demand Diels-Alder reaction of the acyldiene 6 with the silyl enol ether 7 gave the cycloadduct 8 with the required 4 contiguous stereocenters in a single step. This compound was then transformed into the tetracyclic enone 16, which was converted to rhodexin A (1).
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095, United States. jung@chem.ucla.edu
authors.forename: Michael E
authors.initials: ME
authors.lastname: Jung
authors.forename: Dongwon
authors.initials: D
authors.lastname: Yoo
mesh_terms: D000970:Antineoplastic Agents; D002301:Cardiac Glycosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D003500:Cyclization; D006027:Glycosides; D007783:Lactones; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000970:Antineoplastic Agents; D002301:Cardiac Glycosides; D006027:Glycosides; D007783:Lactones; C482684:rhodexin A