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A convenient synthesis of deuterated leukotriene A 4 methyl ester
Author(s) -
Bestmann Hans Jürgen,
Meese Claus O.,
Röder Thomas
Publication year - 1989
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.2580271112
Subject(s) - chemistry , wittig reaction , ylide , propargyl alcohol , alcohol , iodide , reagent , methyl iodide , alkylation , leukotriene c4 , propargyl , medicinal chemistry , organic chemistry , leukotriene , catalysis , medicine , asthma
2,2,3,3‐[ 2 H 4 ]‐1‐Iodopentane ( 8b ) was prepared in four steps from propargyl alcohol and used in the C‐alkylation of the THP‐protected 3‐butyne‐1‐ol ( 10 ). Subsequent protective group removal of 11b, semi‐deuteration of the acetylenic alcohol 12b , and further transformation by known methods afforded the labelled key reagent 3,4,6,6,7,7‐[ 2 H 6 ]‐(Z)‐(3‐nonen‐1‐yl)triphenylphosphonium iodide ( 3b ). Wittig olefination of epoxy dienal 2 with the ylide generated from 3b completed the convenient synthesis of hexadeuterated leukotriene A4 methyl ester ( 1b ).