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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 Styryllactone<sup>1</sup>
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1992
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Bioorganic Chemistry1-Phenyl-5-hexenitols 5/6GlycobiologyOrganic ChemistryChemistryMedicinal ChemistryStereoselective SynthesisAbsolute ConfigurationBiochemistryUnsaturated PolyolsPharmacologyAsymmetric CatalysisNatural Product SynthesisEnantioselective SynthesisBiomolecular EngineeringNatural SciencesPhenylmagnesium Bromide AdditionMedicineSynthetic Chemistry
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.