title: Exploration of cascade cyclizations terminated by tandem aromatic substitution: total synthesis of (+)-schweinfurthin A.
abstract: The termination of epoxide-initiated cascade cyclizations with a range of "protected" phenols is described. When the protecting group can be lost as a stabilized electrophile, the cascade process continues beyond ring closure to afford products which have undergone a tandem electrophilic aromatic substitution. A number of groups have proven viable in this process and the regiochemistry of their substitution reactions has been studied. Application of this methodology in the first total synthesis of (+)-schweinfurthin A, a potent antiproliferative agent, has been achieved.
authors.affiliation: Department of Chemistry, University of Iowa, Iowa City, 52242-1294, USA.
authors.forename: Joseph J
authors.initials: JJ
authors.lastname: Topczewski
authors.forename: John G
authors.initials: JG
authors.lastname: Kodet
authors.forename: David F
authors.initials: DF
authors.lastname: Wiemer
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D013267:Stilbenes / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D000970:Antineoplastic Agents; D004852:Epoxy Compounds; D013267:Stilbenes; C117232:schweinfurthin