6533b7defe1ef96bd1275efd
RESEARCH PRODUCT
Stereoselective Synthesis of 8,12-Furanoeudesmanes from Santonin. Absolute Stereochemistry of Natural Furanoeudesma-1,3-diene and Tubipofurane.
Juan J. SánchezBegoña GarcíaGonzalo BlayJosé R. PedroLuz Cardonasubject
chemistry.chemical_classificationchemistry.chemical_compoundDienechemistryDouble bondStereochemistryOrganic ChemistryAbsolute (perfumery)StereoselectivityEnantiomerCis–trans isomerismCatalysisSantonindescription
Ketobutenolide 3, easily obtained from santonin (1), has been transformed into two natural furanoeudesmanes 4 and 5, isolated from Commiphora molmol and Tubipora musica, respectively. trans- And cis-decalin systems were obtained by stereoselective reduction of the C(4)-C(5) double bond in 3 in the following way: hydrogenation of 3 over Pd/C followed by acidic treatment gave the cis isomer 10 as the major product; selective hydrogenation of the C(1)-C(2) double bond with the Wilkinson's catalyst followed by reduction with NaTeH yielded mainly the trans isomer 9. Compounds 9 and 10 were transformed into 4 and 5 in parallel sequences. Optical rotation and CD measurements of the synthetic products revealed that the stereochemistry of both natural products should be revised to their enantiomeric form.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1996-05-31 | The Journal of organic chemistry |