Just look at the structure of this alkaloid!
Sometimes you just have to step back and marvel at the structures that are found in nature. Check out zamamiphidin A, a new manzamine alkaloid isolated from an Okinawan sponge by J. Kobayashi and co-workers (Organic Letters). Heptacyclic. Quaternary ammonium. Massively bridged. Well done, sponges!
Awesome.
I wonder if you would take out your mercury lamp and shine on it — would it be possible to bridge it even further via an internal [2+2]?
Then ponder over the correct IUPAC name for the desired product.
That would be diabolical. As would the name. I notice the authors didn’t tackle the nomenclature issue. I guess it will be up to someone at CAS when it gets abstracted!
i have wondered for years……why do so many biologically interesting structures of such molecular complexity come (apparently more often) from sponges?? i realize there’s tons of heterocycle diversity/complexity in nature but it seems like a disproportionate number of reports describe sponges as the source for the new yet-to-be-synthesized alkaloid.
I guess when you’re firmly attached to a rock, unable to run from things that want to eat you, you have plenty of time to try new things to defend yourself. Nothing better to do!
plus they get colonized by symbiotic bacteria who are waging chemical warfare against other organisms – this has been apparently going on for long time – multicelular organisms existed in oceans for about 1 billion years, single-cell based ones for at least 3 times as long
Of course, the structure needs to be correct to be that impressive.
Indeed. They rely mainly on NMR. I didn’t see an X-ray determination.