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14 C‐labeling of a novel prostacyclin I 1 derivative, SM‐10902
Author(s) -
Kurosawa Motohiro,
Kanamaru Hiroshi,
Nishioka Kazuhiko
Publication year - 1997
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/(sici)1099-1344(199702)39:2<129::aid-jlcr957>3.0.co;2-w
Subject(s) - chemistry , sodium borohydride , stereoselectivity , yield (engineering) , wittig reaction , ketone , alkoxy group , grignard reaction , derivative (finance) , medicinal chemistry , cerium , organic chemistry , catalysis , reagent , alkyl , materials science , economics , financial economics , metallurgy
(+)‐Methyl [2‐[(2 R ,3a S ,4 R ,5 R ,6a S )‐octahydro‐5‐hydroxy‐4‐[( E )‐(3 S ,5 S )‐3‐hydroxy‐5‐methyl‐1‐[3‐ 14 C]nonenyl]‐2‐pentalenyl]ethoxy]‐acetate ([nonenyl‐3‐ 14 C]SM‐10902) (1) was labeled with carbon‐14 for use in mammalian metabolic studies. The synthesis was achieved in 7 steps from [ 14 C]carbon dioxide: including: 1) Grignard reaction, 2) esterification, 3) condensation with dimethyl methylphosphonate, 4) Wittig‐Horner reaction, 5) separation of isomers by HPLC. Stereoselective reduction of the protected ketone with sodium borohydride in the presence of cerium (III) chloride and subsequent desilylation produced 1. The overall yield was 11.1% from Ba[ 14 C]CO 3 . © 1997 John Wiley & Sons, Ltd.