Summary
Starting from methyl 3-oxo-4-etienate, the authors prepared 17β-hydroxymethyl-4-androsten-3-one and 11β-hydroxy-17β-hydroxymethyl-4-androsten-3-one. Chlorination of 17β-acetoxymethyl-4-androsten-3-one yielded 4-chloro-17β-acetoxymethyl-4-androsten-3-one. 17β-Hydroxymethyl-1, 4-androstadien-3-one was obtained from 17β-hydroxymethyl-4-androsten-3-one, both by chemical and biological methods.
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Während der Durchführung unserer experimentellen Arbeiten erfuhren wir von der Darstellung des 11β-Hydroxy-17β-hydroxymethyl-4-androsten-3-ons (Fp. 205–207°; [α] 19D : + 124° (CH3OH)), des 11β-Hydroxy-17β-acetoxymethyl-4-androsten-3-ons (Fp. 148 bis 159°) und des 17β-Acetoxymethyl-4-androsten-3, 11-dions (Fp. 153–155°; [α]D: + 152,2° (CHCl3):E. Caspi undH. Zajac, J. chem. Soc.1964, 586.
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Schubert, A., Schwarz, S. 17β-Hydroxymethyl-Steroide: Darstellung von Derivaten des 17β-Hydroxymethyl-4-androsten-3-ons. Experientia 21, 688–690 (1965). https://doi.org/10.1007/BF02138472
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DOI: https://doi.org/10.1007/BF02138472