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An efficient synthesis of the crustacean hormone [12‐ 3 H]‐methyl farnesoate and its photolabile analog [13‐ 3 H]‐farnesyl diazomethyl ketone
Author(s) -
Ujváry István,
Prestwich Glenn D.
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.2580280206
Subject(s) - chemistry , ketone , halogenation , labelling , halogen , derivative (finance) , tritium , chemical synthesis , stereochemistry , allylic rearrangement , photoaffinity labeling , alcohol , medicinal chemistry , organic chemistry , catalysis , binding site , biochemistry , financial economics , alkyl , physics , nuclear physics , economics , in vitro
Tritium‐labelled methyl farnesoate ([ 3 H]‐MF, 6.6 Ci/mmol) was prepared from a tritiated allylic alcohol derivative by an efficient new one‐pot halogen exchange‐reductive dehalogenation sequence. The resulting [ 3 H]‐MF was converted in three steps to a diazomethyl ketone analog, [ 3 H]‐FDK, which can be used for the photoaffinity labelling of MF binding proteins.