An efficient synthesis of an 8-phenoxy aporphine derivative utilizing mono-ligated palladium ortho-phenol arylation |
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Authors: | Ghada Ali Gregory D Cuny |
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Institution: | 1. Department of Chemistry, University of Houston, College of Natural Sciences and Mathematics, Houston, TX 77204, United States;2. Department of Pharmacological and Pharmaceutical Sciences, University of Houston, College of Pharmacy, Houston, TX 77204, United States |
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Abstract: | 8-Aryloxy aporphines are a structurally diverse subset of alkaloids that display an array of biological activities. An efficient synthesis of an 8-phenoxy aporphine model compound has been developed utilizing Pictet-Spengler cyclization followed by biaryl bond formation using Pd-XPhos catalyzed ortho-phenol arylation. Biaryl bond formation using direct arylation is also compared. Finally, the stability of the 8-phenoxy aporphine model compound is discussed with potential implications for the isolation, structure elucidation and pharmacognosy of 7-dehydroaporphine natural products. |
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Keywords: | Corresponding author Aporphine 7-Dehydroaporphine Phenoxy Arylation Palladium |
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