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A Synthesis-Driven Structure Revision of ‘Plagiochin E’, a Highly Bioactive Bisbibenzyl
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2009
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Medicinal ChemistryBiosynthesisBioorganic ChemistryBiochemistryPlagiochin ENatural SciencesIsolated BisbibenzylsMolecular BiologyTotal SynthesisNatural Product BiosynthesisStereoselective SynthesisSynthesis-driven Structure RevisionChemical BiologyNatural Product SynthesisHighly Bioactive BisbibenzylSynthetic Chemistry
Recently, a bisbibenzyl named plagiochin E showing remarkable antifungal and antitumor activities was isolated from Marchantia polymorpha, a liverwort. The total synthesis of the proposed structure for plagiochin E and of two structurally and biosynthetically related bisbibenzyls and comparison of the NMR data of the synthetic compounds with those of the isolated bisbibenzyls necessitates a structure revision for plagiochin E. Exemplarily for this metabolite, the stereostructure was investigated, by racemate resolution on a chiral Lux Cellulose-1 phase with HPLC-CD coupling and quantum chemical CD calculations, clearly assigning the P-configuration for the faster and the M-configuration to the slower enantiomer.