Palladium (II)-Catalyzed Oxycarbonylation of Unsaturated Polyols: Synthesis of (-)-Goniofufurone and Assignment of Absolute Configuration to the Natural (+)-Enantiomer, a Cytotoxic Styryllactone1
- 1 January 1992
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1992 (03) , 191-193
- https://doi.org/10.1055/s-1992-21309
Abstract
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.Keywords
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