Word: steroids
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Dates: during 1950-1959
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Like other steroid hormones (e.g., testosterone, androsterone, progesterone), cortisone is a tough chemical customer. Its molecules are built around the steroid nucleus" (TIME, Jan. 29) which has three six-atom carbon rings and one five-atom ring in the proper spatial arrangement. To build such a molecule from scratch was considered so difficult that few chemists ever hoped to accomplish...
...carbon ring and one methyl (CH3) group. Step by step he attached more atoms, carefully choosing his reactions so that the atoms would fall in the proper places. After some 20 laboratory steps, his 22 Ibs. of original raw materials were reduced to 1/28 oz. of a genuine steroid. The compound's molecule has the steroid nucleus with an oxygen atom attached at one end and a carbome-thoxy (C02CH3) group at the other...
...substance is not yet cortisone. He must add another oxygen atom in the proper spot, and must exchange his carbomethoxy group for a dihydroxyacetone sidechain. In the process it will also be necessary to alter the double bonds that now join some of the atoms in his steroid (see diagram). But Chemist Woodward's cautious colleagues agree that the toughest part of the job seems to be over...
...with Woodward's total laboratory synthesis of a steroid from coal tar, it is felt that the starting materials in the interconversions and consequently the desired steroids, will be more available...
Many ways have been worked out already for converting one steroid into another...