title: Asymmetric alcohol C-H allylation and syn-crotylation: C9-C20 of tetrafibricin.
abstract: The C9-C20 segment of the fibrinogen receptor inhibitor tetrafibricin was prepared in 10 steps (longest linear sequence). Ruthenium catalyzed enantioselective syn-crotylation is used to construct C9-C13. Iridium catalyzed asymmetric alcohol C-H allylation of a commercial malic acid derived alcohol is used to construct C14-C20. Recovery and recycling of the iridium catalyst is described.
authors.affiliation: University of Texas at Austin , Department of Chemistry and Biochemistry, Austin, Texas 78712, United States.
authors.forename: Takahiko
authors.initials: T
authors.lastname: Itoh
authors.forename: T Patrick
authors.initials: TP
authors.lastname: Montgomery
authors.forename: Antonio
authors.initials: A
authors.lastname: Recio
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Krische
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D006860:Hydrogen Bonding; D007495:Iridium / Q000737:chemistry*; D018942:Macrolides / Q000737:chemistry* / Q000494:pharmacology; D015394:Molecular Structure; D039341:Receptors, Fibrinogen / Q000037:antagonists & inhibitors* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D018942:Macrolides; D039341:Receptors, Fibrinogen; C082780:tetrafibricin; D007495:Iridium