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A novel strategy to N-Boc-N-methyl--tryptophans (abrine derivatives) was developed that relies on the palladium-catalyzed annulation of ortho-iodoanilines 12 with either N-Boc-N-methyl-propargylglycine 16 or aldehyde 11. Both 11 and 16 can be prepared from d-serine. An alternative route to propargylglycine 16 utilizes an enantioselective propargylation reaction of glycine imine 17.

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Synthesis of <scp>d</scp>-Abrines by Palladium-catalyzed Reaction of ortho-Iodoanilines with <i>N</i>-Boc-<i>N</i>-methylalanyl-substituted Acetaldehyde and Acetylene

Synthesis of d-Abrines by Palladium-catalyzed Reaction of ortho-Iodoanilines with N-Boc-N-methylalanyl-substituted Acetaldehyde and Acetylene