Total Synthesis of Galanthamine and Lycoramine Featuring an Early-Stage C-C and a Late-Stage Dehydrogenation via C-H Activation

被引:29
|
作者
Zhang, Yuna [1 ,2 ]
Shen, Shuna [1 ,2 ]
Fang, Hua [3 ]
Xu, Tao [1 ,2 ]
机构
[1] Ocean Univ China, Key Lab Marine Drugs, Minist Educ, Qingdao 266003, Peoples R China
[2] Ocean Univ China, Sch Med & Pharm, Lab Marine Drugs & Bioprod & Open Studio Druggabi, Pilot Natl Lab Marine Sci & Technol, Qingdao 266003, Peoples R China
[3] Minist Nat Resources, Tech Innovat Ctr Utilizat Marine Biol Resources, Inst Oceanog 3, Xiamen 361005, Peoples R China
关键词
RH-CATALYZED CARBOACYLATION; ASYMMETRIC TOTAL-SYNTHESIS; BOND-CLEAVAGE; HYDROCARBON OXIDATION; EFFICIENT SYNTHESES; (-)-GALANTHAMINE; FUNCTIONALIZATION; OLEFINS; DISEASE; REAGENT;
D O I
10.1021/acs.orglett.9b04337
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, we report a novel strategy toward galanthamine and lycoramine. The concise synthesis was enabled by a Rh-catalyzed gram-scale C-C activation for the tetracyclic carbon framework and a regioselective Pd-catalyzed C-H activation for double-bond introduction. An aqueous-phase Beckmann rearrangement was performed for nitrogen atom insertion. Galanthamine and lycoramine were completed in 11 and 10 steps, respectively.
引用
收藏
页码:1244 / 1248
页数:5
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