Stereoselective synthesis and determination of the cytotoxic properties of spicigerolide and three of its stereoisomers.
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.
Falomir
Eva
E
Departamento de Química Inorgánica y Orgánica, Universidad Jaume I, E-12080 Castellón, Spain.
Murga
Juan
J
Ruiz
Purificación
P
Carda
Miguel
M
Marco
J Alberto
JA
Pereda-Miranda
Rogelio
R
Fragoso-Serrano
Mabel
M
Cerda-García-Rojas
Carlos M
CM
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
D000970:Antineoplastic Agents; D007783:Lactones; C482142:spicigerolide; D012210:Rhamnose