Synthesis · 1999 · 29 citations · 0 references
PharmacyChemistryMedicinal ChemistryBioorganic ChemistryCarbohydrate ChemistryOrganic ChemistryCarbohydrate SynthesisGlycan BiosynthesisGlycosidic Bond FormationMonosaccharide ChemistryOligosaccharide AssemblyOrganic SynthesisGlycopyranose StereochemistryGlycosylation StereochemistryMacrolide GlycosidesNatural Product Total SynthesisStereochemistry Of GlycosidesStereochemistry Of Sugar DerivativesStereoselective GlycosylationStereoselective Sugar Synthesis
The convergent synthesis of macrolide soraphen A1α is described starting from glucose (western part) and mannose (eastern part). Mannose was converted into a 2-deoxyribohexapyranoside that could be methylated and reduced stereoselectively. Chain elongation at C-6 was carried out by stereoselective addition of a magnesium acetylide. The two fragments (western and eastern) were assembled by a Julia olefination followed by macrolactonization. The introduction of the methyl group at C-2 of norsoraphen occurred stereoselectively for thermodynamic reasons.