6533b7dbfe1ef96bd126f7ec
RESEARCH PRODUCT
On the structure of passifloricin A: asymmetric synthesis of the delta-lactones of (2Z,5S,7R,9S,11S)- and (2Z,5R,7R,9S,11S)tetrahydroxyhexacos-2-enoic acid.
J. MurgaJ. Alberto MarcoJorge Garcia‐fortanetMiguel Cardasubject
chemistry.chemical_classificationNatural productEsterificationChemistryStereochemistryOrganic ChemistryEnantioselective synthesisStereoisomerismStereoisomerismRing (chemistry)MetathesisBiochemistryStereocenterFatty Acids Monounsaturatedchemistry.chemical_compoundLactonesCyclizationPyronesStereoselectivityPhysical and Theoretical ChemistryLactonedescription
Stereoselective syntheses of the delta-lactone of (2Z,5S,7R,9S,11S)-tetrahydroxyhexacos-2-enoic acid, the structure reported for passifloricin A, and of its (5R)-epimer are described. The creation of all stereogenic centers relied upon Brown's asymmetric allylation methodology. The lactone ring was created via ring-closing metathesis. The NMR data of both synthetic products, however, were different from those of the natural product. The published structure of passifloricin A is thus erroneous and will require further synthetic work to be unambiguously assigned. [structure: see text]
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2003-04-26 | Organic letters |