title: Synthesis of the C1'-C11' oxazole-containing side chain of leucascandrolide A. Application of a Sonogashira cross-coupling.
abstract: An efficient, convergent synthesis of the C1'-C11' side chain (3) of leucascandrolide A (1) has been achieved. The key bond connection is made through the use of a palladium(0)-catalyzed Sonogashira cross-coupling between trifloyl oxazole (4) and alkynylmetal species (5).
authors.affiliation: Department of Chemistry and Center for Streamlined Synthesis, Metcalf Center for Science and Engineering, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.
authors.forename: Les A
authors.initials: LA
authors.lastname: Dakin
authors.forename: Neil F
authors.initials: NF
authors.lastname: Langille
authors.forename: James S
authors.initials: JS
authors.lastname: Panek
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D000818:Animals; D002384:Catalysis; D003432:Cross-Linking Reagents / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009942:Organometallic Compounds / Q000737:chemistry; D010080:Oxazoles / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D011161:Porifera / Q000737:chemistry*; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013329:Structure-Activity Relationship
chemical_list: D000480:Alkynes; D003432:Cross-Linking Reagents; D009942:Organometallic Compounds; D010080:Oxazoles; D012717:Sesquiterpenes; C408748:leucascandrolide A; D010165:Palladium