title: 5-Hydroxyindoles by intramolecular alkynol-furan diels-alder cycloaddition.
abstract: A convergent approach provides a convenient access to synthetically and biologically useful 3,4-disubstituted 5-hydroxyindoles. The one-pot procedure uses microwave heating to initiate an intramolecular [4 + 2]-cycloaddition of an alkynol segment onto a furan followed by a fragmentation, aromatization, and N-Boc deprotection cascade. Yields range from 15 to 74%, with aromatic substituents providing better conversions. 4-Trimethylsilylated analogues undergo a 1,3-silatropic rearrangement to give the O-TMS ethers.
authors.affiliation: Department of Chemistry and Center for Chemical Methodologies & Library Development, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States.
authors.forename: Matthew
authors.initials: M
authors.lastname: LaPorte
authors.forename: Ki Bum
authors.initials: KB
authors.lastname: Hong
authors.forename: Jie
authors.initials: J
authors.lastname: Xu
authors.forename: Peter
authors.initials: P
authors.lastname: Wipf
mesh_terms: D061565:Cycloaddition Reaction; D005663:Furans / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D005663:Furans; D007211:Indoles; C026785:5-hydroxyindole; C039281:furan