New Radical Approaches to 3-Deoxy-d-oct-2-ulosonic Acids (KDO)

Abstract

Two different approaches, with an unsaturated carbohydrate as a radical acceptor and a carbohydrate derived aldehyde as a radical precursor, led to key intermediates in the synthesis of 3-deoxy-d-oct-2-ulosonic acids (KDO). Manganese(III) acetate and cerium(IV) ammonium nitrate were the reagents of choice for the oxidative generation of radicals, whereas samarium(II) iodide was employed for reductive couplings. Both strategies were realized by using easily available starting materials, with acetic acid as C₂ and ethyl acrylate as C₃ building blocks, respectively.

Key words

carbohydrates - chiral pool - natural products - radical reactions - transition metals

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12

The supplementary crystallographic data for this structure (CCDC 262607) can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/products/csd/request.

15

The supplementary crystallographic data for this structure (CCDC 263264) can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/products/csd/request.