title: Synthesis and Structural Reassignment of Plakinidone.
abstract: In connection with its first synthesis, plakinidone was structurally revised to a five-membered lactone. The key evidence for the previous assignment of this natural product as a perlactone was proven to be a misinterpretation of the MS data because of unawareness of a facile air oxidation. The synthetic samples also allowed for detection of differences in (13)C NMR for diastereomers of remote stereogenic centers, along with the influence of the air oxidation on the optical rotation.
authors.affiliation: State Key Laboratory of Bioorganic and Natural Product Chemistry, Collective Innovative Center for Chemistry and Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
authors.forename: Ze-Jun
authors.initials: ZJ
authors.lastname: Xu
authors.affiliation: State Key Laboratory of Bioorganic and Natural Product Chemistry, Collective Innovative Center for Chemistry and Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
authors.forename: Dong-Xing
authors.initials: DX
authors.lastname: Tan
authors.affiliation: State Key Laboratory of Bioorganic and Natural Product Chemistry, Collective Innovative Center for Chemistry and Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
authors.forename: Yikang
authors.initials: Y
authors.lastname: Wu
mesh_terms: D000818:Animals; D001688:Biological Products / Q000737:chemistry; D004147:Dioxins / Q000138:chemical synthesis / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry; D008386:Marine Biology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010084:Oxidation-Reduction; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D004147:Dioxins; D007783:Lactones; C073643:plakinidone