For a number of reasons, aldosterone is practically never used as a therapeutic agent for correcting electrolytic irregularities in adrenal insufficiency, for which deoxycorticosterone and fludrocortisone are more frequently used.
Deoxycorticosterone: Desoxycorticosterone, 21-hydroxypregn-4-en-3,20-dione acetate (27.2.6), is synthesized in a number of ways, the easiest of which being iodination of progesterone at C21 in the methyl group, and subsequent reaction of the resulting iodo-derivative 27.2.5 with potassium acetate, which leads to formation of the desired desoxycorticosterone in the form of the acetate (27.2.6) .
Another method of synthesizing desoxycorticosterone acetate (27.2.6) is from 3-hydroxy-5,16-pregnadien-20-one. First, the hydroxyl group at C3 must be protected. It undergoes formylation by formic acid, which gives the formate 27.2.7. Reacting this with isopropenylacetate in the presence of p-toluenesulfonic acid gives the enolacetate 27.2.8. Treating the resulting enolacetate with iodosuccinimide, which reacts exclusively with the enolacetate double bond, an iodoketone is formed, which is reacted with potassium acetate to form the acetate 27.2.9. The double bond at C16-C17 is reduced by hydrogen using a palladium on carbon catalyst, forming the product 27.2.10.
Oxidizing this product with aluminum, isopropylate in the presence of cyclohexanone gives desoxycorticosterone acetate (27.2.6) [35,36].
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