Relative configuration of the marine natural product elatenyne using NMR spectroscopic and chemical derivatization methodologies

NMR spectroscopic methodologies used to characterize and elucidate the structure of the marine natural product elatenyne were also applied to the characterization of a new triazole structural derivative of elatenyne, obtained by "Click" chemistry. The two most probable relative configurations assigned to naturally occurring elatenyne were concluded on the basis of key single irradiation nOe NMR enhancements, in combination with the use of a variant of the HSQC NMR experiment that permitted NMR coupling constants to be measured for the overlapped ring junction protons. This study represents the first application of "Click" chemistry to chemically derivatize an unmodified natural product.