Chemistry - A European Journal · 2017 · 29 citations · 39 references
PharmacyChemistryMedicinal ChemistrySynthetic Medicinal ChemistryOrganic SynthesisTarget-oriented SynthesisFuran ChemistryFuran FormationFuran SynthesisKnoevenagel CondensationNatural Product FunctionalizationNatural Product SynthesisNatural Product Total SynthesisTotal Synthesis-derived Analogues
Convergent total syntheses of the furanocembranoids 7-epi-pukalide and 7-acetylsinumaximol B have been achieved using a one-pot Knoevenagel condensation and thioether-mediated furan-forming reaction. Furan formation proceeds via a sulfur ylide and results in rapid introduction of structural complexity during the coupling of two highly functionalised fragments. The targets have been prepared in 16 steps from (R)-perillyl alcohol.
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Jan B. van Beilen, René Holtackers, Daniel Lüscher et al. · Applied and Environmental Microbiology · 2005 · 166 citations · Full text