title: Total syntheses of the resorcylic acid lactone neocosmosin A and its enantiomer.
abstract: A total synthesis of the structure, 1, assigned to the recently reported resorcylic acid lactone (RAL) neocosmosin A has been established. Olefin-cross metathesis, ring-closing metathesis, palladium-catalyzed Meinwald rearrangement, and Mitsunobu esterification reactions were used as key steps. A late-stage and simple modification to the reaction sequence also provided compound ent-1 that, in fact, represents the true structure of the natural product.
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 2601, Australia.
authors.forename: Yiwen
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 2601, Australia.
authors.forename: Michael
authors.initials: M
authors.lastname: Dlugosch
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 2601, Australia.
authors.forename: Martin
authors.initials: M
authors.lastname: Jübermann
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 2601, Australia.
authors.forename: Martin G
authors.initials: MG
authors.lastname: Banwell
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 2601, Australia.
authors.forename: Jas S
authors.initials: JS
authors.lastname: Ward
mesh_terms: D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D012118:Resorcinols / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D007783:Lactones; D012118:Resorcinols; C582805:neocosmosin A