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

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 04期

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

页码：1244 / 1248

页数：5

共 94 条

[91] C-H Bond Functionalization: Emerging Synthetic Tools for Natural Products and Pharmaceuticals [J].