TY - DATA T1 - Asymmetric Total Syntheses of Colchicine, β‑Lumicolchicine, and Allocolchicinoid N‑Acetylcolchinol‑O‑methyl Ether (NCME) PY - 2017/08/19 AU - Xin Liu AU - Ya-Jian Hu AU - Bo Chen AU - Long Min AU - Xiao-Shui Peng AU - Jing Zhao AU - Shaoping Li AU - Henry N. C. Wong AU - Chuang-Chuang Li UR - https://acs.figshare.com/articles/dataset/Asymmetric_Total_Syntheses_of_Colchicine_Lumicolchicine_and_Allocolchicinoid_i_N_i_Acetylcolchinol_i_O_i_methyl_Ether_NCME_/5327455 DO - 10.1021/acs.orglett.7b02224.s002 L4 - https://ndownloader.figshare.com/files/9139132 KW - β- lumicolchicine KW - NCME KW - methyl KW - electrocyclic ring-opening cascade reaction N2 - A 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. ER -