ISSN:
1573-739X
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract Two-dimensional nuclear magnetic resonance was used for the structure elucidation of two isomeric photoproducts of norethisterone, a commonly used progestogen in oral contraceptives. The predominant one of the two isolated products derived from photochemical decomposition of norethisterone upon irradiation with UV-B light (280–320 nm) was 5α,17β-dihydroxy-19-nor-17α-pregn-20-yn-3-one. The minor photoproduct appeared to be the analogous 5β-isomer,i.e. 5β,17β-dihydroxy-19-nor-17α-pregn-20-yn-3-one. The latter compound was also obtained from the thermal reduction of norethisterone-4β,5β-epoxide using aluminium amalgam in isopropanol. Two-dimensional NMR appeared to be superior to mass and IR spectrometry in identifying the isomers.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF02307577
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