title: Modular total syntheses of the marine-derived resorcylic Acid lactones cochliomycins a and B using a late-stage nozaki-hiyama-kishi macrocyclization reaction.
abstract: The natural products cochliomycin A (1) and cochliomycin B (2), two resorcylic acid lactones obtained from marine sources, have been prepared in a concise and stereocontrolled manner from the readily accessible building blocks 4-6. Olefin cross-metathesis, trans-esterification and Nozaki-Hiyama-Kishi (NHK) macrocyclization reactions were employed in the key steps. Hydrolysis of the immediate precursor to cochliomycin B affords the resorcylic acid lactone zeaenol (24).
authors.affiliation: †Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra ACT 2601, Australia.
authors.forename: Benoit
authors.initials: B
authors.lastname: Bolte
authors.affiliation: †Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra ACT 2601, Australia.
authors.forename: Jose A
authors.initials: JA
authors.lastname: Basutto
authors.affiliation: †Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra ACT 2601, Australia.
authors.forename: Christopher S
authors.initials: CS
authors.lastname: Bryan
authors.affiliation: ‡School of Chemistry and Molecular Biosciences, University of Queensland, Brisbane QLD 4072, Australia.
authors.forename: Mary J
authors.initials: MJ
authors.lastname: Garson
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: D001203:Ascomycota / Q000737:chemistry*; D003500:Cyclization; D062385:Hydroxybenzoates / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation
chemical_list: D062385:Hydroxybenzoates; D007783:Lactones; C559005:cochliomycin A; C559006:cochliomycin B