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

[21] Enantioselective Rh-Catalyzed Carboacylation of C=N Bonds via C-C Activation of Benzocyclobutenones [J].

Deng, Lin ;

Xu, Tao ;

Lo, Hongbo ;

Done, Guangbin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (01) :369-374

[22] Direct activation of relatively unstrained carbon-carbon bonds in homogeneous systems [J].

Dermenci, Alpay ;

Coe, Jotham W. ;

Dong, Guangbin .

ORGANIC CHEMISTRY FRONTIERS, 2014, 1 (05) :567-581

[23] Direct aerobic α,β-dehydrogenation of aldehydes and ketones with a Pd (TFA)2/4,5-diazafluorenone catalyst [J].

Diao, Tianning ;

Wadzinski, Tyler J. ;

Stahl, Shannon S. .

CHEMICAL SCIENCE, 2012, 3 (03) :887-891

[24] Synthesis of Cyclic Enones via Direct Palladium-Catalyzed Aerobic Dehydrogenation of Ketones [J].

Diao, Tianning ;

Stahl, Shannon S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (37) :14566-14569

[25] Alzheimer's disease: addressing a twenty-first century plague [J].

Dobson, Christopher M. .

RENDICONTI LINCEI-SCIENZE FISICHE E NATURALI, 2015, 26 (03) :251-262

[26]

Dong G, 2014, TOPICS CURRENT CHEM

[27] Chemoenzymatic Total Synthesis of (+)-Galanthamine and (+)-Narwedine from Phenethyl Acetate [J].

Endoma-Arias, Mary A. A. ;

Hudlicky, Tomas .

CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (41) :14540-14543

[28] Hydrocarbon oxidation vs C-C bond-forming approaches for efficient syntheses of oxygenated molecules [J].

Fraunhoffer, KJ ;

Bachovchin, DA ;

White, MC .

ORGANIC LETTERS, 2005, 7 (02) :223-226

[29] Recent Methodologies That Exploit C-C Single-Bond Cleavage of Strained Ring Systems by Transition Metal Complexes [J].

Fumagalli, Gabriele ;

Stanton, Steven ;

Bower, John F. .

CHEMICAL REVIEWS, 2017, 117 (13) :9404-9432

[30] The Burden of Neurological Disease in the United States: A Summary Report and Call to Action [J].

Gooch, Clifton L. ;

Pracht, Etienne ;

Borenstein, Amy R. .

ANNALS OF NEUROLOGY, 2017, 81 (04) :479-484

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