title: Structural revision of cephalosporolide J and bassianolone.
abstract: The NMR spectra for three "natural" products: cephalosporolide C (Ces-C), cephalosporolide J (Ces-J), and bassianolone were found to be identical, and we proposed that Ces-C was the correct structure for the reported spectra. The first total synthesis of the proposed structure for Ces-J was achieved to support our structural revision for Ces-J. Chemical transformations of bassianolone and computational prediction of (13)C NMR spectra allowed us to conclude that Ces-C was the correct structure for bassianolone. Our synthetic and computational studies suggested that these "different" natural products Ces-C, Ces-J, and bassianolone have the same structure: Ces-C.
authors.affiliation: Department of Chemistry, The Hong Kong University of Science and Technology , Clear Water Bay, Kowloon, Hong Kong, China.
authors.forename: Liyan
authors.initials: L
authors.lastname: Song
authors.forename: Ka-Ho
authors.initials: KH
authors.lastname: Lee
authors.forename: Zhenyang
authors.initials: Z
authors.lastname: Lin
authors.forename: Rongbiao
authors.initials: R
authors.lastname: Tong
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D001688:Biological Products / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D013141:Spiro Compounds; C587752:cephalosporolide C; C000591192:cephalosporolide J; D015107:4-Butyrolactone