Androstanone

Bird TG, PM Fredricks, ERH Jones, GD Meakins (1980) Microbiological hydroxylations. Part 23. Hydroxyl-ations of fluoro-5a-androstanones by the fnngi Calonectria decora, Rhizopus nigricans, and Aspsrgillus ohraceus. J Chem Soc Perkin 1 750-755. 

T.G.C. Bird, P.M. Fredericks, E.R.FI. Jones, G.D. Meakins, Microbiological hydroxylation. Part 23. Flydroxylations of fluoro-5ot-androstanones by the fungi Calonectria decora, Rhizopus nigricans, and Aspergillus ochraceus, J. Chem. Soc. Perkin Trans. 1 (1980) 750-755. 

The 2-formyl derivative (36-4) from androstanone provides the key intermediate for entry to androgens bearing an additional fused heterocyclic ring as well as... 

Hydroxy androstanone Cholestanone, synthetic deriv,s Olhydrocortisone ocetote 41.42 43 44... 

HYDROXY-2-HYDROXYMETHYLENE-17-a-METHYL-3-ANDROSTANONE 17-P-HYDROXY-2-(HYDROXY-METHYLENE)-17-METHYL-5-a-ANDROSTAN-3-ONE ... 

HYDROXYMERCURY)PROPYL)C,MlBAMOYL)PHEN OXY)ACETIC ACID see NCM800 17-p-HYDROXY-2-HYDROXYMETHYLENE-17-a-METHYL-3-ANDROSTANONE see PANIOO 17-p-HYDROXY-2-(HYDROXYMETHYLENE)-l 7-a-METHYL-5-a-ANDROSTAN-3-ONE see PANIOO 17-P-HYDROXY-2-(HYDROXYMETHYLENE)-17-METHYL-5-a-. NDROSEMSI-3-ONE see PANIOO 17-HYDROXY-2-(HYDROXYMETHYLENE)-17-METHYL-5-a-17-P-ANDROSTAN-3-ONE see PANIOO... 

HYDROXYMETHYLENE-17-a-METHYL-5-a-ANDROSTAN-17-P-OL-3-ONE see PANIOO 2-HYDROXYMETHYLENE-l 7-a-METHYL-DIHYDROTESTOSTERONE see PANIOO 2-(HYDROXYMETHYLENE)-17-a-METHYLDIHYDROTESTOSTERONE see P.ANIOO 2-HYDROXYMETHYLENE-17-a-METHYL-17-P-HYDROXY-3-ANDROSTANONE see PANIOO 4-(l-HYDROXY-2-((l-METHYLETHYL)AMINO)ETHYL)-l, 2-BENZENEDIOL see DM "600... 

Alkali metal salts of selenol can also be used in the synthesis of selenol esters. Axial and equatorial selenol esters of cholestane and androstanone have been prepared from the potassium salt (7) and benzoyl chloride (Scheme 2 illustrates the axial isomer). ... 

A -5-Androstadiene-3,17-dione, 461, 462 5 -Androstane-17/S-ol, 377 5a-Androstane-16-one, 243 5< -Androstane-17-one, 243 5a-Androstane-3-one-17fl-ol, 377 Androstanol-3j8, 363 Androstanone-3, 363 A -Androstene-3, 17-dione, 165 A5-Androstene-3/3-ol, 73 A4-Androstene-3,l 1,17-trione, 354 1 Androsterone, 286... 

Figure 7 Preferred sites ofhydroxylation by Calonectria decora in typical 5a-androstanones...

In 1992 Heathcock and Smith developed efficient routes for the synthesis of symmetrical and unsymmetrical bis-steroidal pyrazines from readily available precursors such as 3-cholestanone and androstanone (40). In a later publication they synthesized the unsymmetrical bis-steroidal pyrazines by the reaction of appropriate a-acetoxy ketones with a-amino oximes. Heating either 2/3,17/3-dihydroxyandrostan-3-one diacetate or 2/3-17/3-dihydroxyhecogenin-3-one diacetate with 2-amino-3-methoxyimino-cholestane in toluene at 145°C gave the corresponding symmetrical pyrazine in moderate yields. 

Many of the organic contaminants which were found in Lippe river water were also present in the source samples (see Table 3). The sewage effluent sample and the Seseke river showed the best accordance with the compound spectrum of the Lippe river. However, also in the two tributaries from the rural upper reaches of the river, numerous specific contaminants like 9-methylacridine (No. 8), alkyl phosphates (Nos. 31, 32) and chlorinated alkyl phosphates (Nos. 34, 36) appeared. In the effluent of a pharmaceutical plant, only a few Lippe river contaminants like n-alkanes (No. 1), naphthalene (No. 3), TXIB (No. 21) and caffeine (No. 67) were detected (see Table 3). Therein, mainly structural relatives of androstanone like 3p-hydroxy-5p-androstan-17-one, 3a-hydroxy-5p-androstan-17-one and androstan-50-3,17-dione were present. These compounds are probably by-products of the synthesis of hormone preparations. Some polycyclic aromatic compounds, halogenated compounds and terpenoids were not detected in the source samples (see the underlined compounds in Table 3) and probably have another origin. Representative sampling of various input sources have to be carried out to prove the origin of these compounds. Hexachlorobutadiene (No. 38) and bis(chloropropyl)ethers (No. 44) appear exclusively at the lower reaches of the Lippe river (see Table 1), downstream the chemical plants in Marl. They are attributed to inputs of the chlorochemical industry (see section 3.1). Hence, this suggests their input by an industrial point source. 

Names synonyms ANDROSTERONE cis>androsterone 3ai-hydroxy-17-androstanone androstane-3a>ol> 7 one. FtUOXYMESTERONE 9a fluoro 11 hydroxy 17 methyltesiostcrone 9s>fluoro l I/U7/ >dihydroxy l7a methyi 4-androsten 3 one. ALDOSTERONE electrocorttn 18 oxocorticosterone 18 formyM l/ .2l dthydroxy-4> pregnene>3.20 dione. 

Whereas androstane, cholestane and androstanones can be oxidized in dichloro-methane/acetic acid and even in methanol (see Section II.A.5) the 3- and 17-acetoxy-androstanes as well as 3,17-diacetoxyandrostane resist CH oxidation in this solvent. 5a-Cholestan-3j5-yl acetate is converted in dichloromethane/acetic acid in low yield (5-10%) to tetratrifluoroacetoxy-5a-cholestane-3jS-yl acetate. The side chain at C(i7) is not split off to a noticeable extent. 

The electrolysis of ketosteroids in dichloromethane/methanol does not lead to the oxidation of unactivated CH bonds. With the 3-ketosteroids 5a-androstanone and 5a-cholestan-3-one as substrates besides the acid-catalyzed ketalization of the keto group only chlorination a to the carbonyl group occurs. The anodic oxidation of the 17-keto-steroids 5a-androstan-17-one, 3j -acetoxy-5a-androstan-17-one and 5a-androstan-3,17-dione (21) leads to the opening of the D-ring with the formation of 13,17-secosteroids, which form lactones under the weakly acidic conditions of the electrolysis and work-up (equation... 

The metriod constitutes a novel route to polysubstituted cyclopen-tanones [88], as illustrated here by the synthesis of a precursor of androstanone (38) [89]. 

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