6533b85afe1ef96bd12b9f22

RESEARCH PRODUCT

Total Synthesis of (±)-Scopolamine: Challenges of the Tropane Ring

Pierre-antoine NocquetTill Opatz

subject

010405 organic chemistryChemistryStereochemistryOrganic ChemistryTotal synthesisTropane010402 general chemistryRing (chemistry)01 natural sciencesCycloaddition0104 chemical scienceschemistry.chemical_compoundScopolaminemedicineOrganic chemistryPhysical and Theoretical Chemistrymedicine.drug

description

Scopolamine was synthesized using 6,7-dehydrotropine as a key intermediate. Rhodium-catalyzed [4 + 3] cycloaddition chemistry and a modified Robinson–Schopf reaction were each independently evaluated for their utility in constructing the tropane core. Both synthetic approaches gave comparable overall yields.

yearjournalcountryeditionlanguage
2016-01-29European Journal of Organic Chemistry
https://doi.org/10.1002/ejoc.201501430