title: De Novo Asymmetric Synthesis of Phoracantholide J.
abstract: A de novo asymmetric total synthesis of the macrolide natural product (S)-phoracantholide J has been achieved in 10 steps from the commodity chemicals (1-pentyne, ethyl acrylate, acetaldehyde, and hydrogen). The asymmetry of the route was introduced by a Noyori reduction of a 3-yn-2-one, which makes the route equally amenable to the synthesis of either enantiomer. In addition, this route relies upon an alkyne zipper, a hydroalkynylation, and a macrolactonization to complete the synthesis.
authors.affiliation: Department of Chemistry and Chemical Biology, Northeastern University , Boston, Massachusetts 02115, United States.
authors.forename: Kenneth F
authors.initials: KF
authors.lastname: Avocetien
authors.affiliation: Department of Chemistry and Chemical Biology, Northeastern University , Boston, Massachusetts 02115, United States.
authors.forename: Jiazhen J
authors.initials: JJ
authors.lastname: Li
authors.affiliation: Department of Chemistry and Chemical Biology, Northeastern University , Boston, Massachusetts 02115, United States.
authors.forename: Xiaofan
authors.initials: X
authors.lastname: Liu
authors.affiliation: Department of Chemistry and Chemical Biology, Northeastern University , Boston, Massachusetts 02115, United States.
authors.forename: Yanping
authors.initials: Y
authors.lastname: Wang
authors.affiliation: Department of Chemistry, William Paterson University , 300 Pompton Road, Wayne, New Jersey 07470, United States.
authors.forename: Yalan
authors.initials: Y
authors.lastname: Xing
authors.affiliation: Department of Chemistry and Chemical Biology, Northeastern University , Boston, Massachusetts 02115, United States.
authors.forename: George A
authors.initials: GA
authors.lastname: O'Doherty
mesh_terms: D000818:Animals; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D009942:Organometallic Compounds / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D018942:Macrolides; D009942:Organometallic Compounds; D010165:Palladium; D012428:Ruthenium