Access to 6a-Alkyl Aporphines: Synthesis of (+/-)-N-Methylguattescidine

作者：Ku Angela F; Cuny Gregory D^*

来源：Journal of Organic Chemistry, 2016, 81(20): 10062-10070.

DOI：10.1021/acs.joc.6b02024

(-)-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.

• 出版日期2016-10-21