Access to 6a-Alkyl Aporphines: Synthesis of (±)-N-Methylguattescidine.
(-)-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.
Department of Chemistry and ‡Department of Pharmacological and Pharmaceutical Sciences, University of Houston , Science and Research Building 2, Houston, Texas 77204, United States.
Angela F
AF
Ku
Department of Chemistry and ‡Department of Pharmacological and Pharmaceutical Sciences, University of Houston , Science and Research Building 2, Houston, Texas 77204, United States.
Gregory D
GD
Cuny
D001060:Aporphines / Q000138:chemical synthesis*; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D066244:Proton Magnetic Resonance Spectroscopy; D013237:Stereoisomerism
D001060:Aporphines