6533b86efe1ef96bd12cbcbc

RESEARCH PRODUCT

New Studies and a Reinvestigation on [4+2] Cycloadditions of (−)-Thebaine: Asymmetrical Diels-Alder Reactions with a Conformationally Fixed Chiral Diene

Diana KeilhoferUlf Pindur

subject

chemistry.chemical_classificationThebaineDieneAlkaloidOrganic ChemistryOpiumMedicinal chemistryCycloadditionchemistry.chemical_compoundPolycyclic compoundchemistrymedicineStereoselectivityPhysical and Theoretical ChemistrySelectivitymedicine.drug

description

Some novel Diels-Alder reactions of the opium alkaloid (−)-thebaine (1) as an electron-rich diene and a reinvestigation of its reactions with cyclic and acyclic dienophiles are described. The π-facial selectivity has been studied on the basis of structural analyses of the cycloadducts. Some related results on [4 + 2] cycloaddition reactions of 1-methoxy-1,3-cyclohexadiene (11) are also reported.

yearjournalcountryeditionlanguage
1993-09-13Liebigs Annalen der Chemie
https://doi.org/10.1002/jlac.1993199301151