Potential intermediates in catecholestrogen biosynthesis: Characterization of a dienol epoxide derivative and related compounds via silylation reactions and gas chromatographic/mass spectrometric analysis
✍ Scribed by Samy Abdel-Baky; Philip W. Le Quesne; Edward Schwarz; Paul Vouros
- Publisher
- John Wiley and Sons
- Year
- 1985
- Tongue
- English
- Weight
- 801 KB
- Volume
- 12
- Category
- Article
- ISSN
- 1076-5174
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✦ Synopsis
During 'H-NMR and gas chromatographichnass spectrometric analytical investigations of the enone epoxides 2a-5, which are of interest as tautomers of dienol epoxides implicated in the biosynthesis of catecholestrogens, silylation reactions were observed to yield a derivative 21 of one of the putative dienol epoxide intermediates. The effect of the silylating reagents bis(trimethy1silyl)trifluoroacetamide (BSTFA) and the trimethylsilimidazole (TSIM) on a variety of steroidal ketones, ketols, enones and enone epoxides is discussed and the reaction pathways are compared.