title: Total synthesis of (±)-cycloclavine and (±)-5-epi-cycloclavine.
abstract: Novel routes to the naturally occurring indole alkaloid cycloclavine and its unnatural C(5)-epimer are described. Key features include the rapid construction of the heterocyclic core segments by two Diels-Alder reactions. An indole annulation was accomplished by a late-stage intramolecular Diels-Alder furan cycloaddition, and a methylenecyclopropane dienophile was used for a stereoselective intramolecular [4 + 2] cycloaddition to give the cyclopropa[c]indoline building block present in cycloclavine.
authors.affiliation: Department of Chemistry and Center for Chemical Methodologies and Library Development, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.
authors.forename: Filip R
authors.initials: FR
authors.lastname: Petronijevic
authors.forename: Peter
authors.initials: P
authors.lastname: Wipf
mesh_terms: D003500:Cyclization; D026121:Indole Alkaloids / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D026121:Indole Alkaloids; C560517:cycloclavine