化学
秋水仙碱
全合成
环丙烷
戒指(化学)
组合化学
克
立体化学
产量(工程)
有机化学
生物
内科学
医学
冶金
材料科学
细菌
遗传学
作者
Liang Xiao,Lei Li,Kun Wei,Yu‐Rong Yang
出处
期刊:Organic Letters
[American Chemical Society]
日期:2021-03-18
卷期号:23 (7): 2731-2735
被引量:26
标识
DOI:10.1021/acs.orglett.1c00638
摘要
Herein we report a streamlined, gram-scale total synthesis of (-)-colchicine that takes only 7 easy steps, with an overall yield of 27-36%. To warrant the synthetic efficiency and practicality of (-)-colchicine, we tactically utilized a modified version of a powerful Ir-catalyzed amidation reported by Carreira to install the key chiral C-7 acetamido group, Suzuki and biomimetic phenol oxidative coupling, and Banwell-inspired cyclopropane ring cleavage to construct (-)-colchicine precisely and rapidly. Remarkably, a described strategy also can shorten the synthesis of allocolchicinoid to 4 steps.
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