Synthesis of (±)-aporphine utilizing Pictet-Spengler and intramolecular phenol ortho-arylation reactions |
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| Authors: | Gregory D. Cuny |
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| Affiliation: | Laboratory for Drug Discovery in Neurodegeneration, Brigham & Women's Hospital and Harvard Medical School, 65 Landsdowne St., Cambridge, MA 02139, USA |
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| Abstract: | A synthesis of the alkaloid (±)-aporphine is reported. The initial key step of the synthesis involves a Pictet-Spengler cyclization of N-tosyl tyramine with 2-bromophenylacetaldehyde in trifluoroacetic acid. This step was followed by the second strategic transformation a palladium-mediated intramolecular phenol ortho-arylation reaction utilizing tricyclohexylphosphine as co-catalysts in the presence of cesium carbonate. Finally, de-oxygenation of the phenol, removal of the tosyl group and methylation gave the desired alkaloid. |
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| Keywords: | Pictet-Spengler Palladium ortho-Arylation Phenol Aporphine |
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