Addition of an Apiosyl Radical to Activated Olefins - Synthesis of C-Apiosyl Compounds

Martina Drescher; Friedrich Hammerschmidt

doi:10.1055/s-1996-4407

Synthesis 1996; 1996(12): 1451-1454
DOI: 10.1055/s-1996-4407

paper

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Addition of an Apiosyl Radical to Activated Olefins - Synthesis of C-Apiosyl Compounds

Martina Drescher, Friedrich Hammerschmidt^*

^*Institut für Organische Chemie der Universität Wien, Währingerstraße 38, A-1090 Wien, Austria

Abstract

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3’-O-Benzoyl-2,3-O-isopropylidene-D-apio-β-D-furanosyl bromide (8), prepared in two steps from 2,3-O-isopropylidene-D-apio-β-D-furanose (6), was reacted with tris(trimethylsilyl)silane/AIBN in the presence of an excess of a variety of activated olefins such as dimethyl maleate, methyl acrylate, acrylonitrile, methyl vinyl ketone, crotonaldehyde, cyclopent-2-enone, and cyclohex-2-enone to afford the corresponding C-apiosides 10 having β-configuration.

C-Apiosides 10a-g are prepared from apiosyl bromide 8 via (TMSi)₃SiH/AIBN induced radical addition to activated olefins 9a-g

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