Syntheses of perdeuterated indoles and derivatives as probes for the biosyntheses of crucifer phytoalexins

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.