Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1975-07-28
1976-06-22
Brust, Joseph Paul
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
260404, C07C12146
Patent
active
039651380
ABSTRACT:
A multi-step, stereospecific total synthesis of steroids utilizing intermediates having a cyanoalkyl A-ring precursor is disclosed. The initial starting materials for this process are the relatively inexpensive and commercially available reagents .gamma.-butyrolactone and sodium cyanide. The process is suitable for the preparation of racemic or optically active, medicinally valuable steroids, particularly 19-norsteroids. It is a feature of this process that conditions employed during the multiple step synthesis are selected so as to retain the normally labile nitrile group even during hydrogenation and hydrolysis steps. In this manner, it is possible to employ the nitrile group as an A-ring precursor without resorting to protective groups as was heretofore found necessary in previous steroid total synthesis processes.
REFERENCES:
patent: 2760966 (1956-08-01), Knowles
patent: 2760975 (1956-08-01), Knowles
Cohen Noal
Rosenberger Michael
Saucy Gabriel
Brust Joseph Paul
Gould George M.
Hoffmann-La Roche Inc.
Welt Samuel L.
Wittekind Raymond R.
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