8). The fungus Claviceps purpurea is the causative agent of ergot poisoning, a malady brought on...
8). The fungus Claviceps purpurea is the causative agent of ergot poisoning, a malady brought on by consuming grains (particularly rye) on which the fungus has matured and produced its fruiting bodies. Ergotism has various physiological and neurological effects on humans, notably the skin ailment known as St. Anthony's Fire, as well as involuntary spasms and twitching. The latter ailments have been implicated, in part, in the Salem Witch Trials where the hapless women were cast as witches based on their odd behaviors and visions. The structure at the right is ergotamine, one of the main compounds produced by the fungus. The right side of the structure (dark blue emphasis) is derived from lysergic acid, the main part of the infamous psychoactive drug known as LSD. These fungi seem to know how to mess with the brains of humans. ho Anyway, there are several chiral centers in the structure of ergotamine. A) (8 pts) CIRCLE each chiral carbon in the structure. B) (3 pts) How many possible stereoisomers of ergotamine are possible? C) (4 pts) ASSIGN the R/S designation to the middle carbon, to which the arrow is pointing. Include the priority assignments (1-4).