Carbohydrates as natural chirons: chiral pool strategies toward synthesis of complex natural products.

Abstract

Carbohydrates constitute a rich source of molecular chirality for synthetic chemistry, combining defined stereochemical information, structural diversity, natural occurrence, and readily differentiated functional groups. Carbohydrate-derived building blocks such as D-glucose, D-glucal, D-mannose, deoxyribose, and L-rhamnose serve as chiral-pool precursors for synthesising complex natural products, providing pre-organised stereochemical arrays and orthogonally addressable functionality for constructing densely functionalized molecular architectures. This Review surveys advances reported during 2020-2026 in using carbohydrate-derived chirons to synthesise structurally diverse natural products and advanced intermediates spanning terpenoids, polyketides, alkaloids, macrolides, polyethers, glycolipids, nucleosides, and related bioactive frameworks. Emphasis is placed on their use in the stereocontrolled construction of cyclic ethers, medium-sized carbocycles, heterocyclic motifs, and polycyclic frameworks. Integration of carbohydrate-derived building blocks with ring-closing metathesis, cycloaddition, epoxidation, radical transformations, cross-coupling, and convergent fragment-coupling strategies has enabled concise syntheses of architecturally complex targets with high stereochemical fidelity. Collectively, these studies show how stereochemical information inherent to carbohydrate frameworks can be incorporated into synthetic sequences to prepare structurally complex and biologically relevant molecules.

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