6533b7d9fe1ef96bd126cbc8

RESEARCH PRODUCT

ChemInform Abstract: 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_compoundThebaineDieneChemistryAlkaloidmedicineDiels alderOrganic chemistryOpiumGeneral MedicineSelectivityCycloadditionmedicine.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.

https://doi.org/10.1002/chin.199351267