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Totalsynthese von 18‐oxygenierten Ätiansäuren. Über Steroide, 151. Mitteilung
Author(s) -
Wieland P.,
Heusler K.,
Ueberwasser H.,
Wettstein A.
Publication year - 1958
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.660410214
Subject(s) - chemistry , ketone , hydrogenolysis , formic acid , enol , permanganate , catalysis , organic chemistry , medicinal chemistry , stereochemistry
18‐Substituted etio‐acid derivatives have been prepared from 16‐oxoandrostanes by two methods. The first consists in the condensation with a formic ester, etherification of the hydroxymethylene compound formed, reduction of the 16‐oxo group and acid cleavage to give an α,β‐unsaturated etioaldehyde. By catalytic reduction and oxidation with permanganate the etio‐acid was obtained. Alternatively the 16‐ketone was condensed with diethyl carbonate and the 16‐oxygen function removed by hydrogenolysis of the 16‐enol‐acetate. – The second method was also applied to a Δ 14 ‐16‐ketone of the androstane series.