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Synthetic Studies of Halichondrin B, an Antitumor Polyether Macrolide Isolated from a Marine Sponge. 1. Stereoselective Synthesis of the C1-C13 Fragment<i>via</i>Construction of the B and A Rings by Kinetically and thermodynamically Controlled Intramolecular Michael Reactions.
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1994
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Medicinal ChemistryEnantioselective SynthesisBioorganic ChemistryBiochemistryC1-c13 FragmentNatural SciencesOrganic ChemistryMarine SpongeChemistryCritical StepsChemical BiologyPharmacologyStereoselective SynthesisPharmaceutical ChemistrySynthetic ChemistryHalichondrin BNatural Product Synthesis
A stereoselective synthesis of the C1-C13 fragment of halichondrin B starting from D-glucose is reported. Construction of 2,5-trans (B) and 2,5-cis substituted tetrahydropyran (A) rings using intramolecular Michael reactions under kinetical and thermodynamical conditions, respectively, were the critical steps.