Palladium (II)-Catalyzed Oxycarbonylation of Unsaturated Polyols: Synthesis of (-)-Goniofufurone and Assignment of Absolute Configuration to the Natural (+)-Enantiomer, a Cytotoxic Styryllactone1

Tibor Gracza; Volker Jäger

doi:10.1055/s-1992-21309

Synlett 1992; 1992(3): 191-193
DOI: 10.1055/s-1992-21309

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Palladium (II)-Catalyzed Oxycarbonylation of Unsaturated Polyols: Synthesis of (-)-Goniofufurone and Assignment of Absolute Configuration to the Natural (+)-Enantiomer, a Cytotoxic Styryllactone¹

Tibor Gracza^* , Volker Jäger

^*Institut für Organische Chemie der Julius-Maximilians-Universität Würzburg, Am Hubland, D-8700 Würzburg, Germany

Abstract

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The 3,6-anhydro-2-deoxy-7-phenylglyconolactones (-)-1 and (-)-7 with L-glycero-L-ido and D-glycero-L-ido configuration, respectively, are prepared from monoacetone D-glucose in 6 steps with 11 and 16% yield. Key steps are the phenylmagnesium bromide addition to. unprotected D-xylo-5-hexenose (4), followed by palladium(II)-catalyzed oxycarbonylation of the resulting 1-phenyl-5-hexenitols 5/6. The synthesis of (-)-1 establishes the absolute configuration of the natural antitumor-active goniofufurone (+)-1 as D-glycero-D-ido.

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