title: Synthesis of Illudinine from Dimedone.
abstract: A total synthesis of the illudalane sesquiterpene illudinine was realized in eight steps and 14% overall yield from commercially available dimedone. The approach features tandem fragmentation/Knoevenagel-type condensation and microwave-assisted oxidative cycloisomerization to establish the isoquinoline core. Completion of the synthesis involves a recently reported cascade SNAr/Lossen rearrangement on a densely functionalized aryl bromide and an optimized procedure for O-methylation of 8-hydroxyisoquinolines. The oxidative cycloisomerization proceeds by way of a novel inverse-demand intramolecular dehydro-Diels-Alder cycloaddition, which has a potentially broader appeal for preparing substituted isoquinolines.
authors.affiliation: Department of Chemistry and Biochemistry, Florida State University , Tallahassee, Florida 32306, United States.
authors.forename: Alec E
authors.initials: AE
authors.lastname: Morrison
authors.affiliation: Department of Chemistry and Biochemistry, Florida State University , Tallahassee, Florida 32306, United States.
authors.forename: Tung T
authors.initials: TT
authors.lastname: Hoang
authors.affiliation: Department of Chemistry and Biochemistry, Florida State University , Tallahassee, Florida 32306, United States.
authors.forename: Mélodie
authors.initials: M
authors.lastname: Birepinte
authors.affiliation: Department of Chemistry and Biochemistry, Florida State University , Tallahassee, Florida 32306, United States.|C. Eugene Bennett Department of Chemistry, West Virginia University , Morgantown, West Virginia 26506, United States.
authors.forename: Gregory B
authors.identifier: 0000-0001-6133-3747
authors.initials: GB
authors.lastname: Dudley