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C−H Acetoxylation‐Based Chemical Synthesis of 17 β‐Hydroxymethyl‐17 α‐methyl‐18‐norandrost‐13‐ene Steroids
Author(s) -
Hurski Alaksiej L.,
Barysevich Maryia V.,
Dalidovich Tatsiana S.,
Iskryk Marharyta V.,
Kolasava Nastassia U.,
Zhabinskii Vladimir N.,
Khripach Vladimir A.
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201602957
Subject(s) - hydroxymethyl , ene reaction , stereocenter , chemistry , steroid , metabolite , stereochemistry , palladium , combinatorial chemistry , organic chemistry , catalysis , enantioselective synthesis , hormone , biochemistry
Palladium‐catalyzed C−H acetoxylation has been proposed as a key transformation in the first chemical synthesis of steroids bearing a unique 17β‐hydroxymethyl‐17α‐methyl‐18‐nor‐13‐ene D ‐fragment. This C−H functionalization step was crucial for inverting the configuration at the quaternary stereocenter of a readily available synthetic intermediate. The developed approach was applied to prepare the metandienone metabolite needed as a reference substance in anti‐doping analysis to control the abuse of this androgenic anabolic steroid.