title: Cephalosporolide B serving as a versatile synthetic precursor: asymmetric biomimetic total syntheses of cephalosporolides C, E, F, G, and (4-OMe-)G.
abstract: Cephalosporolide B (Ces-B) was efficiently synthesized and exploited for the first time as a versatile biomimetic synthetic precursor for the chemical syntheses of not only cephalosporolides C, G, and (4-OMe-) G via a challenging diastereoselective oxa-Michael addition but also the structurally unprecedented cephalosporolides E and F via a novel biomimetic ring-contraction rearrangement. These findings provide the first direct chemical evidence that Ces-B may be the true biosynthetic precursor of cephalosporolides.
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: Yuan
authors.initials: Y
authors.lastname: Liu
authors.forename: Rongbiao
authors.initials: R
authors.lastname: Tong
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D032701:Biomimetics; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D007783:Lactones; D013141:Spiro Compounds; C585639:cephalosporolide B; C587752:cephalosporolide C; C540295:cephalosporolide E; C540296:cephalosporolide F; C545906:cephalosporolide G; D015107:4-Butyrolactone