Journal
TETRAHEDRON LETTERS
Volume 53, Issue 44, Pages 5828-5832Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2012.07.110
Keywords
Pyrrole-aminoimidazole (PAI); Axinella sp.; Marine sponges; Pre-axinellamine
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Funding
- ICSN-CNRS
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Two novel dimeric pyrrole-aminoimidazole (PAI) alkaloids (-) donnazoles A-B (1-2) were isolated from the marine sponge Axinella donnani collected off the Mauritius Island. Their structures were elucidated mainly by 2D NMR. Both compounds bear the crucial substituted cyclopentane of 'pre-axinellamine', the hypothetical common intermediate of all dimeric PAIs. Additionally, the essential trans-6,7 ring junction of palau'amine's congeners is already established in 1 and 2. The absolute configurations of 1 and 2 were deduced via NOE correlations in combination with the comparison of their circular dichroism data with the one of (-) sceptrin. The absolute configuration of (-) donnazoles A (1) and B (2) is coherent with the absolute configuration of the known dimeric members of PAI alkaloids. (C) 2012 Elsevier Ltd. All rights reserved.
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