Oximes are unrecognized chameleons in general and specialized plant metabolism. and -hydroxyphenylacetaldehyde oxime are key intermediates in the biosynthesis of the cyanogenic glucoside dhurrin produced in sorghum. Nevertheless, none of the geometrical oxime isomers accumulate in the plant. Herein, we report a convenient route to the chemical synthesis of and -hydroxyphenylacetaldehyde oxime and its biologically produced -β-d-glucopyranoside using -hydroxyphenylacetic acid as a starting material. This starting material is also available in radiolabeled forms. All reaction steps proceeded with excellent yield under mild conditions, operational facility, and scalability.
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A Convenient Route to Large-Scale Chemical Synthesis of -Hydroxyphenylacetaldehyde Oxime and Its -β-d-Glucopyranoside: Key Intermediates and Products in Plant Specialized Metabolism.
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