Concepedia

Synthetic Studies of Halichondrin B, an Antitumor Polyether Macrolide Isolated from a Marine Sponge. 3. Synthesis of C27-C36 Subunit<i>via</i>Completely Stereoselective<i>C</i>-Glycosylation to the F Ring

K. HORITA, Y. SAKURAI, M. NAGASAWA, S. Hachiya, Osamu Yonemitsu

Synlett · 1994 · 41 citations · 0 references

Concepts

Natural SciencesChemistryMedicinal ChemistryCarbohydrate ChemistryOrganic ChemistrySynthetic Medicinal ChemistryMacrocycle SynthesisMarine Bioactive CompoundsMarine Drug DiscoveryRetrosynthetic AnalysisAnticancer Marine CompoundsBioactive Compounds From Marine SpongesGlycosylation MechanismsMarine Sponge MetabolitesMarine Sponge Natural Product BiosynthesisSponges As Drug SourcesStereocontrolled Library SynthesisStereoselective Synthesis

Abstract

A stereoselective synthesis of the C27-C36 fragment of halichondrin B starting from L-tartaric acid using an efficient acidcatalyzed C-glycosylation to the F ring as the key step is reported.