A Synthesis-Driven Structure Revision of ‘Plagiochin E’, a Highly Bioactive Bisbibenzyl

Abstract 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 compar...

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Published in:Synlett 2009-07, Vol.2009 (11), p.1852-1858
Main Authors: Speicher, Andreas, Groh, Matthias, Zapp, Josef, Schaumlöffel, Anu, Knauer, Michael, Bringmann, Gerhard
Format: Article
Language:English
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Summary:Abstract 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.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0029-1217510