Construction of 1,6-anhydro-functionalized carbohydrate-fused spiro-chromanones via intramolecular domino/spirocyclization.
Publication/Presentation Date
6-1-2025
Abstract
The synthetic protocol for the first synthesis of carbohydrate-fused spiro-chromanones via intramolecular domino reaction between o-hydroxyacetophenones and dihydrolevoglucosenone (DHL) is described. The reactions proceed via the formation of an acetophenone (APh) enamine intermediate when performed in the presence of pyrrolidine in ethanol. The formation of a new carbon-carbon bond between nucleophilic carbon of the enamine of APh and C-2 of DHL is followed by cyclization, producing a new six-membered ring, as the result of an intramolecular domino process. Several substituted o-hydroxyacetophenones were reacted. The structure of products was determined using
Volume
552
First Page
109466
Last Page
109466
ISSN
1873-426X
Published In/Presented At
Jankowski, N., Hager, C., Arcure, H., Lopez, J., Barrios Gomez, A. M., Witczak, Z. J., Bielski, R., & Mencer, D. E. (2025). Construction of 1,6-anhydro-functionalized carbohydrate-fused spiro-chromanones via intramolecular domino/spirocyclization. Carbohydrate research, 552, 109466. https://doi.org/10.1016/j.carres.2025.109466
Disciplines
Medicine and Health Sciences | Pharmacy and Pharmaceutical Sciences
PubMedID
40179538
Department(s)
Department of Pharmacy
Document Type
Article