6533b851fe1ef96bd12a98eb
RESEARCH PRODUCT
Stereoselective synthesis and determination of the cytotoxic properties of spicigerolide and three of its stereoisomers.
Purificacion RuizCarlos M. Cerda-garcía-rojasJ. Alberto MarcoMiguel CardaJuan MurgaRogelio Pereda-mirandaMabel Fragoso-serranoEva Falomirsubject
StereochemistryRhamnoseStereoisomerismAntineoplastic AgentsMetathesisChemical synthesisRhamnosechemistry.chemical_compoundLactonesStructure-Activity RelationshipCell Line TumorCytotoxic T cellStructure–activity relationshipOrganic chemistryHumanschemistry.chemical_classificationCell DeathChemistryorganic chemicalsOrganic ChemistryStereoisomerismGeneral MedicineSpicigerolideAldoseCyclizationOrgan SpecificityStereoselectivityLactonedescription
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2003-11-25 | The Journal of organic chemistry |