title: Formal synthesis of (±)-methyl rocaglate using an unprecedented acetyl bromide mediated Nazarov reaction.
abstract: To date the prototype Nazarov cyclization of a cross-conjugated pentadienone to the core structure of the rocaglate natural products has not been successful (9 into 12). It has been found that this conversion can be achieved by the use of acetylbromide in excellent yield and results in a strategically very direct route to these antitumor agents.
authors.affiliation: Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, Texas 78712, USA. p.magnus@mail.utexas.edu
authors.forename: Philip
authors.initials: P
authors.lastname: Magnus
authors.forename: Wesley A
authors.initials: WA
authors.lastname: Freund
authors.forename: Eric J
authors.initials: EJ
authors.lastname: Moorhead
authors.forename: Trevor
authors.initials: T
authors.lastname: Rainey
mesh_terms: D000085:Acetates / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000494:pharmacology; D001572:Benzofurans / Q000737:chemistry*; D002626:Chemistry, Pharmaceutical / Q000379:methods; D003432:Cross-Linking Reagents / Q000737:chemistry; D003500:Cyclization; D008956:Models, Chemical; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry; D010936:Plant Extracts / Q000378:metabolism; D013237:Stereoisomerism
chemical_list: D000085:Acetates; D000970:Antineoplastic Agents; D001572:Benzofurans; D003432:Cross-Linking Reagents; D010936:Plant Extracts; C483989:methyl rocaglate; C412887:acetyl bromide; D010100:Oxygen