09 June 2011

#SmilesC Answer 8

  • #SmilesC whose degradation is used to prepare this compound? CC(=O)C1CCC2C1(C)CCC3C4(C)CCC(=O)C=C4CCC23
The compound is called progesterone with wikipedia explaining,
"Progesterone ... (pregn-4-ene-3,20-dione) is a C-21 steroid hormone involved in the female menstrual cycle, pregnancy (supports gestation) and embryogenesis of humans and other species. Progesterone belongs to a class of hormones called progestogens, and is the major naturally occurring human progestogen."
The degradation is called the Marker degradation, a method of getting into steroid chemistry from a relatively cheap starting material. It's an impressive piece of chemistry, as are the subsequent transformations to other steroids.
But the real reason for posting the questions was to bring up the name of Russel Marker. There are many stories about Russel Marker, here's the begining of one,
"Russell Marker hated wasting time. Upon qualifying for a doctoral degree in chemistry as a twenty-three-year-old student at the University of Maryland in 1925, all that stood between him and his degree were several required physical chemistry courses. But Marker didn't want to take physical chemistry, as he already had a master's degree in the subject. The university refused to modify its graduation requirements and Marker's own advisor threatened him with the dead end career of "urine analyst" if he didn't complete his coursework. Marker refused and left the university without his degree, an independent scientist in search of a job."
Follow the link to find out what happened next.

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