KÃ¶ck and Grube.Â ACIEE, 2007, EarlyView. DOI: 10.1002/anie.200604076.
An interesting debate has sprung up in the comments on this little beastie (thanks for the tip, folks!), as several groups around the world are working on palau’amine as a target. However, this Angewantde reports the isolation of a family member, tetrabromostyloguanidine, with different relative stereochemistry. Most interestingly, the deviation appears to be centred on the ring junction on the fused saturated 5,5 rings – with a trans ring junction in the newly isolated product. The NMR evidence in itself is convincing, and the molecular modeling adds to that opinion, so perhaps it’s time for a rethink?