title: Total synthesis of odoamide, a novel cyclic depsipeptide, from an Okinawan marine cyanobacterium.
abstract: Odoamide is a novel cyclic depsipeptide with highly potent cytotoxic activity isolated from the Okinawan marine cyanobacterium Okeania sp. It contains a 26-membered macrocycle composed of a fatty acid moiety, a peptide segment and isoleucic acid. Four possible stereoisomers of the odoamide polyketide substructure were synthesised using a chiral pool approach. The first total synthesis of odoamide was also successfully achieved. The structure of synthetic odoamide was verified by comparing its NMR spectra with those of the natural product.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan. soishi@pharm.kyoto-u.ac.jp.
authors.forename: Masato
authors.initials: M
authors.lastname: Kaneda
authors.affiliation: Faculty of Education, University of the Ryukyus, Nishihara, Okinawa 903-0213, Japan.
authors.forename: Kosuke
authors.initials: K
authors.lastname: Sueyoshi
authors.affiliation: Faculty of Education, University of the Ryukyus, Nishihara, Okinawa 903-0213, Japan.
authors.forename: Toshiaki
authors.initials: T
authors.lastname: Teruya
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan. soishi@pharm.kyoto-u.ac.jp.
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Ohno
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan. soishi@pharm.kyoto-u.ac.jp.
authors.forename: Nobutaka
authors.initials: N
authors.lastname: Fujii
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan. soishi@pharm.kyoto-u.ac.jp.
authors.forename: Shinya
authors.identifier: http://orcid.org/0000-0002-2833-2539
authors.initials: S
authors.lastname: Oishi
mesh_terms: D000072283:A549 Cells; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D049109:Cell Proliferation / Q000187:drug effects; D000458:Cyanobacteria / Q000737:chemistry*; D047630:Depsipeptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D009369:Neoplasms / Q000188:drug therapy; D061065:Polyketides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D000970:Antineoplastic Agents; D047630:Depsipeptides; D061065:Polyketides