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Methods for the synthesis of carbon‐13 labelled acids and esters
Author(s) -
Jordan Angela C.,
Axford Lorraine C.,
Harding John R.,
O'Connell Yvonne,
Simpson Thomas J.,
Willis Christine L.
Publication year - 2007
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.1198
Subject(s) - chemistry , knoevenagel condensation , stereoselectivity , aldol condensation , aldol reaction , derivative (finance) , stereochemistry , cinnamic acid , organic chemistry , acetylation , catalysis , biochemistry , financial economics , economics , gene
Syntheses of isotopically labelled putative biosynthetic intermediates to the natural products monocerin 1 , hectochlorin 2 and strobilurin A 3 are described. For the preparation of [9,10‐ 13 C 2 ]dihydroisocoumarin 10 , a stereoselective aldol condensation of 13 C 2 ‐acetylated chiral auxiliary 5 was used to assemble the labelled C9‐C14 fragment. The preferred approaches to the syntheses of [1,2‐ 13 C 2 ]5,5‐dichlorohexanoic acid 15 and the N ‐acetylcysteamine derivative of [1,2‐ 13 C 2 ]cinnamic acid 19 involved a Horner‐Wadsworth‐Emmons chain extension and Knoevenagel reaction, respectively. Copyright © 2007 John Wiley & Sons, Ltd.
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