ChemicalBook CAS DataBase List ALDOSTERONE

ALDOSTERONE synthesis

6synthesis methods

Product Name:ALDOSTERONE
CAS Number:52-39-1
Molecular formula:C21H28O5
Molecular Weight:360.45

Aldosterone, 11β,21-dihydroxypregn-4-en-2,18,20-trione (27.2.4), is synthesized from 21-O-acetylcorticosterone, which when reacted with nitrosyl chloride in pyridine gives the nitrite 27.2.1. When photochemically irradiated, this compound is transformed to the oxime 27.2.2, which is hydrolyzed by nitrous acid and forms the semiacetal 27.2.3, which is an acetate of the desired aldosterone. Alkaline hydrolysis of the acetyl group of this compound leads to the desired aldosterone (27.2.4) .

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Yield:-

Steps:

Multi-step reaction with 5 steps
1: chromium (VI)-oxide; acetic acid
2: methanol; concentrated aqueous hydrochloric acid
3: ethylene glycol; toluene-4-sulfonic acid / 0.2 Torr
4: dioxane; lithium alanate; diethyl ether
5: aqueous HCl

References:

v. Euw et al. [Helvetica Chimica Acta,1955,vol. 38,p. 1423,1436]

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