Configurational analysis of tetracyclic dimeric pyrrole-imidazole alkaloids using a floating chirality approach.

J Nat Prod

Alfred-Wegener-Institut für Polar- und Meeresforschung in der Helmholtz-Gemeinschaft, Am Handelshafen 12, D-27570 Bremerhaven, Germany.

Published: February 2012

The structure elucidation of the palau'amine congener tetrabromostyloguanidine (1), which used interproton distances from ROESY spectra as restraints in a computational approach, the so-called fc-rDG/DDD method, led to a revision of the relative configuration of palau'amine (2) and its congeners in 2007. The recent total synthesis of (±)-palau'amine (2) subsequently confirmed the computed structural revision of the relative configuration. In order to test a broader application range of the fc-rDG/DDD method, the present study investigated two additional dimeric pyrrole-imidazole alkaloids, axinellamine A (3) and 3,7-epi-massadine chloride (4). These calculations allowed the simultaneous assignment of the relative configuration for all eight stereogenic centers of compounds 3 and 4 without using any information from the reported configurations. In contrast to the palau'amine congeners, the fc-rDG/DDD method confirmed the relative configuration originally described for axinellamine A (3) and 3,7-epi-massadine chloride (4).

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3315375PMC
http://dx.doi.org/10.1021/np200514gDOI Listing

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