ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Steroids. XLVI. Preparation of 15,16,17-Trisubstituted Steroids by Ring Cleavage of 17β-Substituted 15β,16β-Epoxy-estra-1,3,5(10)-triene 3-MethylethersThe ring cleavage of 15β.16β-epoxy-3-methoxy-estra-1-3,5(10)-triene-17β-ol 1a with strong nucleophiles occurs mainly at C-16, yielding 16α-substituted 15β,17β-diols 2a-f. Besides this, 1a is cleaved to a small extent at C-15, yielding the 15α-substituted 16β,17β-diols 3a - f and the Δ14-16,17β-diol 5a. The structures have been elucidated by means of i.r., H-n.m.r. and mass spectroscopy.
Notes:
Die Ringöffnung von 15β.16β-Epoxy-3-methoxy-östra-1.3.5(10)-trien-17β-ol 1a mit starken Nucleophilen erfolgt vorzugsweise am C-16 unter Bildung der 16α-substituierten 15β.17β-Diole 2a - 2f. Daneben wird 1a in geringem Umfang am C-15 unter Bildung der 15α-substituierten 16β.17β-Diole 3a-3f und des Δ14-16.17β-Diols 5a gespalten. Die Strukturaufklärung erfolgt mit Hilfe der IR-, 1H-NMR- und Massenspektroskopie.
Additional Material:
4 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19763180213
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