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The synthesis of 13‐ cis ‐retinoic acid‐ 6 , 7 ‐ 14 C
Author(s) -
Muccino Richard R.,
Wasiowich Carol A.
Publication year - 1980
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.2580170317
Subject(s) - chemistry , citral , wittig reaction , reagent , retinoic acid , acetone , stereochemistry , dioxolane , grignard reagent , medicinal chemistry , organic chemistry , biochemistry , chromatography , essential oil , gene
A route to crystalline 13‐ cis ‐retinoic acid‐ 6 , 7 ‐ 14 C ( 1 ) has been developed. Addition of acetylene‐ 1 , 2 ‐ 14 C to 6‐methyl‐5‐hepten‐2‐one ( 4 ) gave dehydrolinalool‐ 1 , 2 ‐ 14 C ( 5 ) which was catalytically transformed into citral‐ 1 , 2 ‐ 14 C ( 6 ) and then condensed with acetone to give pseudoionone‐ 4 , 5 ‐ 14 C ( 7 ). Ring closure of 7 gave β‐ionone‐ 6 , 7 ‐ 14 C ( 8 ) which upon addition of vinyl Grignard give vinyl‐β‐ionol‐ 6 , 7 ‐ 14 C ( 9 ). Conversion of 9 to its triphenylphosphonium salt 10 and condensation of the Wittig reagent from 10 with 4‐hydroxy‐3‐methylbut‐2‐enolide ( 11 ) gave a mixture from which pure 13‐ cis ‐retinoic acid‐ 6 , 7 ‐ 14 C ( 1 ) could be crystallized.