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Structure of pithecolobine. III. The synthesis of the 1,5- and 1,3-desoxypithecolobines
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1968
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Combinatorial ChemistryMedicinal ChemistryPharmaceutical ScienceBioorganic ChemistryBiochemistryBioassay-guided IsolationRelated AnaloguesNatural SciencesMedicineMass SpectrometryChemical Degradation.the SynthesisChromatographyStereoselective SynthesisChemical BiologyPharmacologyPharmaceutical ChemistryDrug DiscoveryNatural Product Synthesis
The second communication of this series has shown that "pithecolobine" is a family of closely related analogues represented by the general formula 1. In the present paper a crude semiquantitative estimate of the individual components is achieved by a combination of vapor-phase chromatography and chemical degradation.The synthesis of the desoxypithecolobines 3a and 3b and their tetratosylates 11a and b11b is described. A comparison of these compounds with the corresponding "natural" mixtures by thin-layer chromatography in several systems, infrared, nuclear magnetic resonance, and mass spectrometry was found to support strongly the conclusions reached by the previous degradative work.