期刊
ORGANIC LETTERS
卷 23, 期 7, 页码 2731-2735出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c00638
关键词
-
资金
- Key Research Program of the Frontier Sciences of the CAS [QYZDB-SSW-SMC026, ZDBS-LY-SM030]
- National Natural Science Foundation of China [21971249, 22001256]
The streamlined gram-scale total synthesis of (-)-colchicine reported here is efficient and practical, using various reactions to rapidly construct the compound, while also shortening the synthesis of allocolchicinoid.
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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