Construction of 1,6-anhydro-functionalized carbohydrate-fused spiro-chromanones via intramolecular domino/spirocyclization

IF 2.4 3区化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY

Carbohydrate Research Pub Date : 2025-03-28 DOI:10.1016/j.carres.2025.109466

Nicole Jankowski , Christopher Hager , Holly Arcure , Jessie Lopez , Any M. Barrios Gomez , Zbigniew J. Witczak , Roman Bielski , Donald E. Mencer

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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 ¹H and ¹³C NMR, GC-MS and X-ray crystallography. The yields are good to excellent (62–92 %), and the products are crystalline and easy to isolate. So far, the synthesized compounds were tested only for their antifungal properties. The results were disappointing.

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来源期刊

Carbohydrate Research 化学-生化与分子生物学

CiteScore

5.00

自引率

3.20%

发文量

183

审稿时长

3.6 weeks

期刊介绍： Carbohydrate Research publishes reports of original research in the following areas of carbohydrate science: action of enzymes, analytical chemistry, biochemistry (biosynthesis, degradation, structural and functional biochemistry, conformation, molecular recognition, enzyme mechanisms, carbohydrate-processing enzymes, including glycosidases and glycosyltransferases), chemical synthesis, isolation of natural products, physicochemical studies, reactions and their mechanisms, the study of structures and stereochemistry, and technological aspects. Papers on polysaccharides should have a "molecular" component; that is a paper on new or modified polysaccharides should include structural information and characterization in addition to the usual studies of rheological properties and the like. A paper on a new, naturally occurring polysaccharide should include structural information, defining monosaccharide components and linkage sequence. Papers devoted wholly or partly to X-ray crystallographic studies, or to computational aspects (molecular mechanics or molecular orbital calculations, simulations via molecular dynamics), will be considered if they meet certain criteria. For computational papers the requirements are that the methods used be specified in sufficient detail to permit replication of the results, and that the conclusions be shown to have relevance to experimental observations - the authors'' own data or data from the literature. Specific directions for the presentation of X-ray data are given below under Results and "discussion".