SYNTHESIS OF 4-HYDROXY-15-OXAANDROST-4-EN-3-ONE AND OTHER POTENTIAL AROMATASE INHIBITORS FROM SANDARACOPIMARIC ACID

The stereoselective synthesis of 4-substituted androstenes (8 beta,14 alpha) 30 and 36 related to inhibitors of the enzyme aromatase and 5 alpha-reductase has been achieved in a short-step sequence from sandaracopimaric acid. The synthetic strategy is the stereoselective construction of ring D. and...

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Bibliographic Details
Published inJ. Chem. Soc., Perkin Trans. 1 no. 5; pp. 569 - 576
Main Authors MARTIN, MB, MATEOS, AF, GONZALEZ, RR
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 1995
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CHEMISTRY
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Summary:The stereoselective synthesis of 4-substituted androstenes (8 beta,14 alpha) 30 and 36 related to inhibitors of the enzyme aromatase and 5 alpha-reductase has been achieved in a short-step sequence from sandaracopimaric acid. The synthetic strategy is the stereoselective construction of ring D. and the appropriate modification of the A-ring diterpene functionality to the enone system found in the aromatase inhibitors. A parallel sequence is developed to obtain the isomers (8 alpha,14 beta) 31 and 41.
ISSN:0300-922X
1364-5463
DOI:10.1039/p19950000569