6533b823fe1ef96bd127f3e4
RESEARCH PRODUCT
Influence of conformational factors on acid-catalyzed cyclizations of germacranolides: Molecular structure of the cyclization products of gallicin and 8α-hydroxygallicin (shonachalin a)
Juan F. Sanz-cerveraVicente García-llisoJ. Alberto MarcoLuis R. DomingoMiguel CardaJohann LexFernando López-ortizSantiago Rodriguezsubject
GermacranolideStereochemistryChemistryAcid catalyzedOrganic ChemistryMoleculeOrganic chemistryGeneral ChemistryPhysical and Theoretical Chemistrydescription
Acid-catalyzed cyclization of the natural germacranolide gallicin (8) yielded, among other products, the 1,4-epoxyeudes-manolide 9, which has a trans-fused decaline system. Under the same conditions the closely related germacranolide shonachalin A (8α-hydroxygallicin) (3) cyclized to the eudesmanolide 4 with a cis fused decaline system. The structures of these cyclization products were secured by means of chemical correlations and X-ray diffraction analyses.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1995-10-01 | Liebigs Annalen |