6533b7dbfe1ef96bd126f79a
RESEARCH PRODUCT
Stereoselective Synthesis of the Antiprotozoal Lactone Passifloricin A and Seven Isomers Thereof
Miguel CardaJuan MurgaJorge Garcia‐fortanetJ. Alberto Marcosubject
medicine.drug_classStereochemistryAntiprotozoal AgentsMolecular ConformationConjugated systemChemical synthesisAldehydeMass SpectrometryLactoneschemistry.chemical_compoundIsomerismmedicineOrganic chemistrychemistry.chemical_classificationNatural productMolecular StructureNatural compoundOrganic ChemistryAbsolute configurationEnantioselective synthesisStereoisomerismGeneral MedicineEnantiopure drugchemistryPyronesAntiprotozoalStereoselectivityOxidation-ReductionLactonedescription
The conjugated delta-lactone passifloricin A, a natural product with antiprotozoal activity, and seven isomers thereof have been synthesized in enantiopure form. It has been shown in this way that the proposed structure for the natural compound was erroneous. The correct structure is now evidenced. Key steps of the syntheses were asymmetric Brown-type aldehyde allylations and ring-closing metatheses.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2004-10-09 | The Journal of Organic Chemistry |