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Updated: Aug 18, 2026

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
Published on: April 27, 2017
Access to 6a-Alkyl Aporphines: Synthesis of (±)-N-Methylguattescidine
1Department of Chemistry and ‡Department of Pharmacological and Pharmaceutical Sciences, University of Houston , Science and Research Building 2, Houston, Texas 77204, United States.
Abstract:
(-)-N-Methylguattescidine (3) is an alkaloid recently isolated from Fissistigma latifolium and assigned as a rare example of a 6a-alkyl aporphine. Herein, we report the synthesis of (±)-3 and the des-hydroxyl derivative 4 using our previously reported ortho-phenol arylation methodology mediated by the XPhos precatalyst as a key synthetic step. In addition, substituents on the aryl halide portion of the ortho-phenol arylation substrates significantly influenced the formation of an oxidized side product.
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