title: Sequential [3 + 2] and [4 + 2] cycloadditions for stereoselective synthesis of a novel polyheterocyclic scaffold.
abstract: A strategy of combining [3 + 2] cycloaddition and intramolecular Diels-Alder reaction is developed for the synthesis of a novel polycyclic scaffold with skeletal and substitutional diversities. Intermediates generated from stereoselective [3 + 2] cycloaddition of azomethine ylides and maleimides were derivatized for intramolecular Diels-Alder reaction of furan to form highly condensed heterocyclic products as racemic single diastereomers.
authors.affiliation: Department of Chemistry, University of Massachusetts Boston , 100 Morrissey Boulevard, Boston, Massachusetts 02125, United States.
authors.forename: Qing
authors.initials: Q
authors.lastname: Lu
authors.forename: Xin
authors.initials: X
authors.lastname: Huang
authors.forename: Gonghua
authors.initials: G
authors.lastname: Song
authors.forename: Chung-Ming
authors.initials: CM
authors.lastname: Sun
authors.forename: Jerry P
authors.initials: JP
authors.lastname: Jasinski
authors.forename: Amanda C
authors.initials: AC
authors.lastname: Keeley
authors.forename: Wei
authors.initials: W
authors.lastname: Zhang
mesh_terms: D001391:Azo Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D061565:Cycloaddition Reaction; D008301:Maleimides / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D013882:Thiosemicarbazones / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D001391:Azo Compounds; D008301:Maleimides; D013882:Thiosemicarbazones; C512188:azomethine