title: Stereoselective synthesis and determination of the cytotoxic properties of spicigerolide and three of its stereoisomers.
abstract: Stereoselective syntheses of the naturally occurring, cytotoxic lactone spicigerolide and three nonnatural stereoisomers thereof are described. The commercially available sugar l-rhamnose was in all cases the chiral starting material. Key steps in each of these syntheses were asymmetric Brown allylations and ring-closing metatheses. The cytotoxic activities of the four lactones against a range of tumoral lines were then determined.
authors.affiliation: Departamento de Química Inorgánica y Orgánica, Universidad Jaume I, E-12080 Castellón, Spain.
authors.forename: Eva
authors.initials: E
authors.lastname: Falomir
authors.forename: Juan
authors.initials: J
authors.lastname: Murga
authors.forename: Purificación
authors.initials: P
authors.lastname: Ruiz
authors.forename: Miguel
authors.initials: M
authors.lastname: Carda
authors.forename: J Alberto
authors.initials: JA
authors.lastname: Marco
authors.forename: Rogelio
authors.initials: R
authors.lastname: Pereda-Miranda
authors.forename: Mabel
authors.initials: M
authors.lastname: Fragoso-Serrano
authors.forename: Carlos M
authors.initials: CM
authors.lastname: Cerda-García-Rojas
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D016923:Cell Death / Q000187:drug effects; D045744:Cell Line, Tumor; D003500:Cyclization; D006801:Humans; D007783:Lactones / Q000138:chemical synthesis* / Q000494:pharmacology; D009928:Organ Specificity; D012210:Rhamnose / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D007783:Lactones; C482142:spicigerolide; D012210:Rhamnose