title: Intramolecular Diels-Alder and tandem intramolecular Diels-Alder/1,3-dipolar cycloaddition reactions of 1,3,4-oxadiazoles.
abstract: The scope of intramolecular Diels-Alder and a novel tandem Diels-Alder/1,3-dipolar cycloaddition cascade of 1,3,4-oxadiazoles is disclosed. In the cases examined, the tandem cycloadditions construct three new rings with formation of four new C-C bonds and set all six stereocenters about a central six-membered ring in a single step including three contiguous and four total quaternary centers without a trace of a second diastereomer.
authors.affiliation: Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
authors.forename: Gordon D
authors.initials: GD
authors.lastname: Wilkie
authors.forename: Gregory I
authors.initials: GI
authors.lastname: Elliott
authors.forename: Brian S J
authors.initials: BS
authors.lastname: Blagg
authors.forename: Scott E
authors.initials: SE
authors.lastname: Wolkenberg
authors.forename: Danielle R
authors.initials: DR
authors.lastname: Soenen
authors.forename: Michael M
authors.initials: MM
authors.lastname: Miller
authors.forename: Scott
authors.initials: S
authors.lastname: Pollack
authors.forename: Dale L
authors.initials: DL
authors.lastname: Boger
mesh_terms: D003500:Cyclization; D010069:Oxadiazoles / Q000737:chemistry*; D014747:Vinblastine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*
chemical_list: D010069:Oxadiazoles; C009667:vindoline; D014747:Vinblastine