ol7b02224_si_002.cif (188.59 kB)
Asymmetric Total Syntheses of Colchicine, β‑Lumicolchicine, and Allocolchicinoid N‑Acetylcolchinol‑O‑methyl Ether (NCME)
dataset
posted on 2017-08-19, 00:00 authored by Xin Liu, Ya-Jian Hu, Bo Chen, Long Min, Xiao-Shui Peng, Jing Zhao, Shaoping Li, Henry N. C. Wong, Chuang-Chuang LiA concise
and highly enantioselective synthesis of colchicine (>99% ee) in eight steps and 9.3% overall yield, without the need
for protecting groups, was developed. A unique Wacker oxidation was
used for enabling regioselective construction of the highly oxidized
and synthetic challenging tropolone C-ring. Furthermore, asymmetric
syntheses of β-lumicolchicine and N-acetylcolchinol-O-methyl ether (NCME) were achieved. Notably, NCME was synthesized
from β-lumicolchicine by an unusual decarbonylation and electrocyclic
ring-opening cascade reaction.