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Stereochemically Reliable Syntheses of Pachastrissamine and Its 2-epi-Congener via Oxazolidinone Precursors from an Established Starting Material N-tert-Butoxycarbonyl-Protected Phytosphingosine
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2012
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Bioorganic ChemistryEngineeringOrganic ChemistryChemistryTotal SynthesesDiversity Oriented SynthesisStereoselective SynthesisOxazolidinone PrecursorsBiochemistryDiversity-oriented SynthesisPharmacologyNatural Product SynthesisPentadecyl MethanesulfonateEnantioselective SynthesisBiomolecular EngineeringReliable SynthesesNatural SciencesMaterial N-tert-butoxycarbonyl-protected PhytosphingosineSynthetic Chemistry
Efficient, stereochemically unambiguous, total syntheses of pachastrissamine and its 2-<i>epi</i>-congener from the readily available common precursor (1<i>R</i>)-1-{(4<i>S</i>,5<i>S</i>)-2-oxo-4-[(tritylÂoxy)methyl]-1,3-oxazolidin-5-yl}pentadecyl methanesulfonate are reported. Syntheses of (3a<i>S</i>,6<i>R</i>,6a<i>R</i>)- and (3a<i>S</i>,6<i>S</i>,6a<i>R</i>)-6-tetradecylhexahydro-2<i>H</i>-cyclopenta[<i>d</i>][1,3]oxazol-2-one by this route have unambiguously resolved a dispute over the structures of these products.