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Syntheses of perdeuterated indoles and derivatives as probes for the biosyntheses of crucifer phytoalexins
Author(s) -
Pedras M. Soledade C.,
Okinyo Denis P. O.
Publication year - 2006
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.1028
Subject(s) - chemistry , crucifer , nitrobenzene , indole test , deuterium , stereochemistry , organic chemistry , botany , physics , biology , catalysis , quantum mechanics
A simple two‐step preparation of [ 2 H 4 ]indole, a starting material necessary for the synthesis of various crucifer metabolites, starting with readily available 1 H NMR solvent [ 2 H 5 ]nitrobenzene (99% deuterated) was developed. [4,5,6,7‐ 2 H 4 ]Indole 99% deuterated at the specified positions was then used to synthesize [4′,5′,6′,7′‐ 2 H 4 ]indolyl‐3‐acetaldoxime, [4′,5′,6′,7′‐ 2 H 4 ]1‐methoxyindolyl‐3‐acetaldoxime, [1″,1″,1″,4′,5′,6′,7′‐ 2 H 7 ]1‐methoxyindolyl‐3‐acetaldoxime, [4′,5′,6′,7′‐ 2 H 4 ]1‐methoxybrassinin, and [3,3,3,4′,5′,6′,7′‐ 2 H 7 ]1‐methoxybrassinin. Copyright © 2005 John Wiley & Sons, Ltd.