jo6b02024_si_001.pdf (5.53 MB)
Access to 6a-Alkyl Aporphines: Synthesis of (±)‑N‑Methylguattescidine
journal contribution
posted on 2016-09-30, 17:55 authored by Angela
F. Ku, Gregory D. Cuny(−)-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.