Upjohn started with the stigmasterol in soybeans to synthesize many of their steroids via n-hydroxy-progesterone. However, the stigmasterol first had to be separated from the related sitosterol in the soybeans. The sitosterol had no use and tons of it accumulated over the years until a huge pile of it was a highly-visible feature at the back of the Upjohn Portage site. This pile defied repeated attempts to utilize it but eventually Upjohn developed a biocatalytic process to convert the sitosterol into a precursor for synthesizing steroids. The two photos below show how large it had become. The person on the top of the pile is Dr. Doug Livingston, one of the authors on a key patent, along with Prof. Scott Denmark and Dr. Bruce Pearlman. Livingston is posed on his skis as if he was going to ski down that "mountain" of sterol.
More detail on this and other steroid chemistry is in the presentations at the
2019 May 2019 celebration where the American Chemical Society
(ACS) granted National Historic Chemical Landmark Status to
Kalamazoo. This was for steroid chemistry achievements of scientists who
worked at The Upjohn Company during the years 1950-1990. |