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The synthesis of isotopically labeled retinoids
Author(s) -
Liebman Arnold A.,
Burger Walter,
Malarek David H.,
Serico Lucia,
Muccino Richard R.,
Perry Clark W.,
Choudhry Satish C.
Publication year - 1990
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580280505
Subject(s) - chemistry , tritium , wittig reaction , butenolide , retinoic acid , hydrolysis , metabolite , stereochemistry , acetylation , alkaline hydrolysis , organic chemistry , radiochemistry , biochemistry , physics , nuclear physics , gene
Retinyl acetate ( 4a ) has been prepared with a tritium label at the C‐11 and C‐12 positions by partial reduction of oxenin ( 1 ) with tritium gas followed by acetylation and rearrangement. Specific activities of up to 40 curies/mmole have been attained. By alkaline hydrolysis, retinol ( 5 ) has been obtained and derivatized as one of several retinyl esters or has been oxidized to all‐ trans retinoic acid ( 6 ) having equally high specific tritium activities. From beta ionone ( 12 ), 13‐ cis retinoic acid ( 10 ) has been elaborated in a variety of isotopically labeled forms. A key reaction in the sequence, the Wittig coupling of the triphenylphosphonium derivative of vinyl beta ionol ( 15a‐c ) and the butenolide, 5‐hydroxy‐4‐methyl‐2(5H)‐furanone ( 8 ), provides access to 13‐ cis retinoic acid and its 4‐oxo metabolite labeled with either isotopic hydrogen or carbon.