title: Catalytic asymmetric synthesis of palmerolide A via organoboron methodology.
abstract: A catalytic enantioselective synthesis of the antimelanoma marine natural product (-)-palmerolide A was accomplished using a longest sequence of 21 steps and without resorting to stoichiometric chiral auxiliaries or the chiral pool. The right half was constructed with a new variant of the Claisen-Ireland rearrangement exploiting an alkenylboronate as a masked hydroxyl. The left half featured the first application of a diol.SnCl(4)-catalyzed enantioselective crotylboration in the context of a complex target. This distinct strategy could pave the way to the design of simplified analogues of palmerolide.
authors.affiliation: Department of Chemistry, University of Alberta, Edmonton, AB T6G 2G2, Canada.
authors.forename: Marlin
authors.initials: M
authors.lastname: Penner
authors.forename: Vivek
authors.initials: V
authors.lastname: Rauniyar
authors.forename: Ludwig T
authors.initials: LT
authors.lastname: Kaspar
authors.forename: Dennis G
authors.initials: DG
authors.lastname: Hall
mesh_terms: D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001896:Boron Compounds; D018942:Macrolides; C522534:palmerolide A