Radical Cyclisation Reactions leading to Doubly Branched Carbohydrates and 6- and 8-Oxygenated 2,9-Dioxabicyclononane Derivatives

Article abstract of DOI:10.1039/c39890001247

2,3-Dideoxy-α-D-erythro-hex-2-enopyranosyl derivatives having, separately, 2-halogenoethyl substituents at O-1 and O-4, on treatment with tri-n-butyltin hydride together with a radical promoter, gave products with tetrahydrofuranyl rings cis-fused to C-1, C-2 and C-3, C-4, i.e. with branched-points at C-2 and C-3, respectively, and similar reactions in the presence of methyl acrylate or allyltributyltin gave main products with the same bicyclic structures but with additional branch points at C-3 and C-2; when applied to a 2-bromo-1-methoxyethyl 2,3-dideoxyhex-2-enopyranoside and to a 2-bromoethyl 3-deoxyhex-2-enopyranoside the ring closure reactions afforded 8- and 6-oxygenated 2,9-dioxabicyclo<4.3.0>nonane derivatives.

Full text of DOI:10.1039/c39890001247

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