Reichstein’s compound

It grew out of another discovery in the senior author s laboratory, namely, that Reichstein s compound S could be converted in high yield into 11-epicortisol (1) by the enzymes of fungi of the genus Aspergillus The conversion of this inactive substance into the hormone cortisol thus became a problem of considerable importance. A route involving the 9,11-dehydro steroid (3) readily prepared from 11-epicortisol via its 21-acetate 11-tosylate... 

IjS-Hydroxylation was reported for Reichstein s Compound S (1) with Rhizoctonia ferruge-... 

Other fungal species have been employed for the 2/i-hydroxylation of Reichstein s Compound S" (3), e.g., Rhizoctonia ferrugena75,95, Helminthosporium tritici vulgaris96, Sclerotinia libertiana97 and Laclarius quietus9. ... 

Steroid compounds (127) have been obtained (524) by condensing several iodo analogs of Reichstein s compound with N-alkyl (or aryl) thioureas in acetonic solution (Scheme 61), with X = or O, R = Et, Pr, iPr, n-Bu, s-Bu, Ph, p-MeOCgH4, p-EtOC6H4, p-MeCgH4, m-MeC H4, m-ClQH4, 3,5-Cl2C[Pg.129]

Aside from cortisone and 17a-hydroxycorticosterone, there have been isolated from beef adrenals six corticosteroids containing five oxygen atoms which are usually considered biologically inactive but which have been available in such minute amounts that only very cursory physiological investigations have been carried out with them. Of these six, only one, allopregnane-3a,ll/3,17a,21-tetrol-20-one (Reichstein s Compound C), has never been synthesized. Principally in connection with the various syntheses of cortisone, there have been developed preparative procedures for the other five inactive steroids, and it may be hoped that they will now be subjected to more careful biological scrutiny. 

Improved preparation of cortisone from Reichstein s Compound S. 

In this context, two processes now have useful and practical application in the pharmaceutical industry. The first one is the synthesis of a cortisone analogue, prednisolone, which is used as a drug against rheumatoid arthritis. A steroid precursor, Reichstein s compound, is passed through a series of two different columns, each containing a specific enzyme attached to a polyacrylamide polymer support (128). The hydroxylation reaction at the prochiral C-11 position occurs with retention of configuration. 

Desoxyoorticosterone (DOC) Reichstein s compound S 21-Hydroxyprogesterone 17o-Hydroxydesoxycorticosterone Debydrocorticosterone 21-Hydroxy-A<-pregnene- 17o,21-Dihydroxy-A<-pregnene- 21-Hydroxy-A -pregnene-... 

---