A synthesis of this molecule by Du Bois uses a rhenium-catalyzed C-H insertion to create oxazolidinones. The first synthesis of this compound by Kishi
A synthesis of this molecule by Du Bois uses a rhenium-catalyzed C-H insertion to create oxazolidinones. The first synthesis of this compound by Kishi and Goto used a Diels-Alder reaction with an oxime and a Beckmann rearrangement to synthesize the skeleton, followed by a pair of epoxidations. Isobe's synthesis uses a Claisen rearrangement and Sonogashira coupling to create cyclohexane, then used an Overmann rearrangement to add nitrogen. Its biosynthesis is dependent on symbiotic bacteria in the ovaries and gallbladder of organisms secreting it, and might begin with linking isopentyl-PP and adipose sugar to arginine. This compound contains guanidinium bound to a pyrimidine, along with five hydroxyl-containing rings in the main body. Similar to STX, this compound binds to the opening of fast-current sodium channels, where it remains for tens of seconds; this inhibits contraction of cardiac muscle. Ten thousand times deadlier than cyanide, for 10 points, name this neurotoxin that causes paralysis and death, famously found in pufferfish.
A synthesis of this molecule by Du Bois uses a rhenium-catalyzed C-H insertion to create oxazolidinones.
{Tetrodotoxin} or {TTX}