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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