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Total synthesis of isoquinocyclinone
Mike Dischmann1, Timo Frassetto, M André Breuning
1Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße, 35043 Marburg (Deutschland), Fax: (+49) 6421-2825677.
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.

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