title: Tandem ring-closing metathesis/isomerization reactions for the total synthesis of violacein.
abstract: A series of 5-substituted 2-pyrrolidinones was synthesized through a one-pot ruthenium alkylidene-catalyzed tandem RCM/isomerization/nucleophilic addition sequence. The intermediates resulting from RCM/isomerization showed reactivity toward electrophiles in aldol condensation reactions which provided a new entry for the total synthesis of the antileukemic natural product violacein.
authors.affiliation: Department of Chemistry, Technical University of Denmark, DK-2800 Kgs. Lyngby, Denmark.
authors.forename: Mette T
authors.initials: MT
authors.lastname: Petersen
authors.forename: Thomas E
authors.initials: TE
authors.lastname: Nielsen
mesh_terms: D000475:Alkenes / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D007211:Indoles; D012428:Ruthenium; C063155:violacein