Citation: Pengwei Chen, Xian Ma, Ni Song, Jianjun Wang, Han Ding, Peng Wang, Hongzhi Cao, Xue-Wei Liu, Zhihua Lv, Ming Li. Synthesis of alduronic acid lactones and rare sugar glyconolactones via decarboxylative oxygenation of uronic acids: Construction of polyhydroxylated fused-ring alkaloids[J]. Chinese Chemical Letters, ;2025, 36(11): 110983. doi: 10.1016/j.cclet.2025.110983 shu

Synthesis of alduronic acid lactones and rare sugar glyconolactones via decarboxylative oxygenation of uronic acids: Construction of polyhydroxylated fused-ring alkaloids

Pengwei Chen ^{a, 1} ,
Xian Ma ^{a, 1} ,
Ni Song ^{a, b} ,
Jianjun Wang ^a ,
Han Ding ^{a, c} ,
Peng Wang ^a ,
Hongzhi Cao ^{a, b} ,
Xue-Wei Liu ^{a, c} ,
Zhihua Lv ^{a, b} ,
Ming Li ^{a, b, *,}

a.
Key Laboratory of Marine Drugs of Ministry of Education, Shandong Key Laboratory of Glycoscience and Glycotherapeutics, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China
b.
Laboratory for Marine Drugs and Bioproducts, Qingdao Marine Science and Technology Center, Qingdao 266237, China
c.
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, Singapore 637371, Singapore

lmsnouc@ouc.edu.cn

Received Date: 20 November 2024
Revised Date: 11 February 2025
Accepted Date: 19 February 2025
Available Online: 20 February 2025

Figures(6)

Alduronic acid lactones and glyconolactones are highly functionalized and versatile chiral building blocks. Herein, we describe a novel approach to these compounds via decarboxylative oxygenation of uronic acids. The transformations proceed using Selectfluor and TEMPO as oxidants, either in the presence of catalytic amounts of Ag₂CO₃ or in the absence of this catalyst. The methodology provides structurally diverse alduronic acid lactones and enables the preparation of rare sugar glyconolactones from easily available D-C-glycosides. Based on the ¹⁸O-labeling experiments, control experiments, and isolation of the key intermediates, a radical-polar crossover reaction mechanism is proposed. The utility of this method is demonstrated through efficient conversions of alduronic acid lactones into polyhydroxylated cyclic alkaloids and castanospermine-type architectures.
- Decarboxylative oxygenation,
- Alduronic acid lactones,
- Glyconolactones,
- Uronic acids,
- Alkaloids
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