title: Total synthesis of isoquinocyclinone.
abstract: The total synthesis of the heptacyclic natural product isoquinocyclinone has been achieved. A Hauser annulation was used to assemble the anthraquinone core structure. The unique 2,4,5,6-tetrahydropyrrolo[2,3-b]pyrrole substructure was prepared by alkyne addition to a lactone intermediate and subsequent Ni(0) -mediated cyanide addition, the conversion of an O,O- into an N,O-acetal, and final intramolecular N-alkylation.
authors.affiliation: Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße, 35043 Marburg (Deutschland), Fax: (+49) 6421-2825677.
authors.forename: Mike
authors.initials: M
authors.lastname: Dischmann
authors.forename: Timo
authors.initials: T
authors.lastname: Frassetto
authors.forename: M André
authors.initials: MA
authors.lastname: Breuning
authors.forename: Ulrich
authors.initials: U
authors.lastname: Koert
keywords: Hauser annulation; acetals; isoquinocyclinone; natural products; total synthesis