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Methods for the synthesis of carbon-13 labelled acids and esters

✍ Scribed by Angela C. Jordan; Lorraine C. Axford; John R. Harding; Yvonne O'Connell; Thomas J. Simpson; Christine L. Willis

Publisher: John Wiley and Sons
Year: 2007
Tongue: French
Weight: 96 KB
Volume: 50
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.1198

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✦ Synopsis

Abstract

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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