The biogenesis of the manzamines was initially baffling, although the recent ingenious suggestion of an intramolecular Diels-Alder reaction in a macrocyclic bisdihydropyridine, though not yet confirmed in the laboratory, is entirely plausible. We now describe the structure of kauluamine (1), which was isolated from an Indonesian sponge Prianos sp. It is an unsymmetrical manzamine dimer, thus adding yet another level of complexity to this fascinating group of alkaloids.
This document is the accepted manuscript version of a published work that appeared in final form in Journal of the American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/ja00148a017. This article may be cited as: Ohtani, I. I., Ichiba, T., Isobe, M., Kelly-Borges, M., & Scheuer, P. J. (1995). Kauluamine: an unprecedented manzamine dimer from an Indonesian marine sponge, Prianos sp. Journal of the American Chemical Society, 117(43), 10743-10744. doi:10.1021/ja00148a017
Florida Atlantic University. Harbor Branch Oceanographic Institute contribution #1129.