Document Detail

Synthesis of 3 alpha, 5 alpha-tetrahydroaldosterone.
MedLine Citation:
PMID:  6748646     Owner:  NLM     Status:  MEDLINE    
3 alpha, 5 alpha-Tetrahydroaldosterone (12a), a metabolite of aldosterone, has been synthesized from the lactone 2a or, preferably 11 beta, 21-dihydroxy-5-pregnene-3,20-dione-18-oic acid 3,20-di-(ethylene glycol)-ketal (18----11) lactone 21-acetate (6b), via 11 beta, 21-dihydroxy-5 alpha-pregnane-3,20-dione-18-oic acid 3,20-di-(ethylene glycol) ketal (18----11) lactone 21-acetate (4b). Selective hydrolysis of the latter at C-3 furnished the monoketal 5 which, on reduction with potassium tri-sec-butylborohydride, yielded predominantly 3 alpha, 11 beta, 21-trihydroxy-5 alpha-pregnan-20-one-18-oic acid 20-(ethylene glycol)-ketal (18----11) lactone (8a) and its acetate 8b. Further reduction with diisobutylaluminum hydride afforded 3 alpha, 5 alpha-tetrahydroaldosterone-20-ketal (10a), which was directly hydrolyzed to 12a with dilute acid in tetrahydrofuran-dioxan. Periodate oxidation led to the gamma-etiolactone 14a, which was then further converted into 5 alpha-dihydroaldosterone-gamma-etiolactone (14c).
M Harnik; Y Kashman; D J Morris
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Journal of steroid biochemistry     Volume:  20     ISSN:  0022-4731     ISO Abbreviation:  J. Steroid Biochem.     Publication Date:  1984 Jun 
Date Detail:
Created Date:  1984-08-29     Completed Date:  1984-08-29     Revised Date:  2008-11-21    
Medline Journal Info:
Nlm Unique ID:  0260125     Medline TA:  J Steroid Biochem     Country:  ENGLAND    
Other Details:
Languages:  eng     Pagination:  1313-20     Citation Subset:  IM    
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MeSH Terms
Aldosterone / analogs & derivatives*,  chemical synthesis*
Chemical Phenomena
Indicators and Reagents
Magnetic Resonance Spectroscopy
Mass Spectrometry
Spectrophotometry, Infrared
Reg. No./Substance:
0/Indicators and Reagents; 13489-75-3/tetrahydroaldosterone; 52-39-1/Aldosterone

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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