Falomir Eva, Murga Juan, Ruiz Purificación, Carda Miguel, Marco J Alberto, Pereda-Miranda Rogelio, Fragoso-Serrano Mabel, Cerda-García-Rojas Carlos M
Departamento de Química Inorgánica y Orgánica, Universidad Jaume I, E-12080 Castellón, Spain.
J Org Chem. 2003 Jul 11;68(14):5672-6. doi: 10.1021/jo034470y.
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.
