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Synthesis of Steroids from... Mexican yams?

Tack

Well-known member
I was reading some articles. And found this to be pretty amusing.
The pharmacological importance of many natural steroids has stimulated much synthetic work in an effort to obtain practical quantities of naturally occurring and unnatural steroids. Oftentimes a combination of biosynthesis and organic synthesis works best. For example, the need for large quantities of cortisone derivatives for therapeutic use in treatment of arthritis and similar metabolic diseases has led to intensive research on synthetic approaches for methods of producing steroids with oxygen functions at C11, which is not a particularly common point of substitution in steroids.

An efficient way of doing this is by microbiological oxidation. Cortisone can be manufactured on a relatively large scale from the saponin, diosgenin, which is isolated from tubers of a Mexican yam of the genus Dioscorea. Diosgenin is converted to progesterone, then by a high-yield (80%-90%) oxidation with the mold, Rhizopus nigricans, to 11-hydroxyprogesterone and finally to cortisone:

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John D. Robert and Marjorie C. Caserio (1977) Basic Principles of Organic Chemistry, second edition. W. A. Benjamin, Inc. , Menlo Park, CA. ISBN 0-8053-8329-8
 
I like a nice nice set of gams… oh wait… you said yams… the tatters.
 
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