Rh-Catalyzed [3+2] Cycloaddition of 1-Sulfonyl-1,2,3-triazoles: Access to the Framework of Aspidosperma and Kopsia Indole Alkaloids

被引：61

作者：

Li, Yun ^{[1
,2
]}

Zhang, Qingyu ^{[1
]}

Du, Qiucheng ^{[1
]}

Zhai, Hongbin ^{[1
,3
]}

机构：

[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China

[3] Peking Univ, Shenzhen Grad Sch, Sch Chem Biol & Biotechnol, Lab Chem Genom, Shenzhen 518055, Peoples R China

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 16期

基金：

中国国家自然科学基金;

关键词：

TERMINAL ALKYNES; CYCLIZATION/CYCLOADDITION CASCADE; ENANTIOSELECTIVE SYNTHESIS; NATURAL-PRODUCTS; TRANSANNULATION; ANNULATION; TRIAZOLES; STRATEGY; PYRROLES; PYRROLOINDOLINES;

D O I：

10.1021/acs.orglett.6b01968

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Rh(II)-catalyzed dearomative intramolecular [3 + 2] dipolar cycloaddition involving the indolic C2-C3 carbon-carbon double bond has been developed. The reaction was launched from the triazole moiety within the substrate and proceeded efficiently under mild conditions., A wide range of functional groups could be tolerated. These features render the current reaction a highly useful tool for the synthesis of polycyclic indole alkaloids, as showcased by a rapid assembly of the core structure of Aspidosperma and the related alkaloids.

引用

页码：4076 / 4079

页数：4

共 57 条

[1] Highly enantioselective synthesis of chiral imides and derived products via chiral base desymmetrisation [J].

Adams, DJ ;

Blake, AJ ;

Cooke, PA ;

Gill, CD ;

Simpkins, NS .

TETRAHEDRON, 2002, 58 (23) :4603-4615

[2] Enantioselective organocatalytic construction of pyrroloindolines by a cascade addition-cyclization strategy: Synthesis of (-)-flustramine B [J].

Austin, JF ;

Kim, SG ;

Sinz, CJ ;

Xiao, WJ ;

MacMillan, DWC .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) :5482-5487

[3] MDR reversal by deprenylated tetracyclic and hexacyclic analogues of N-acetylardeemin:: Confirmation of the ardeemin pharmacophore [J].

Avendano, Carmen ;

Caballero, Esmeralda ;

Mendez-Vidal, Cristina ;

de Quesada, Ana R. ;

Carlos Menendez, J. .

LETTERS IN DRUG DESIGN & DISCOVERY, 2006, 3 (06) :369-377

[4] Synthesis of strychnine [J].

Bonjoch, J ;

Solé, D .

CHEMICAL REVIEWS, 2000, 100 (09) :3455-3482

[5] A general synthetic entry to the pentacyclic Strychnos alkaloid family, using a [4+2]-cycloaddition/rearrangement cascade sequence [J].

Boonsombat, Jutatip ;

Zhang, Hongjun ;

Chughtai, Majid J. ;

Hartung, John ;

Padwa, Albert .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (09) :3539-3550

[6] Rh(II)-catalyzed intramolecular dearomatizing annulation of N-sulfonyl-1,2,3-triazoles: synthesis of polycyclic spiroindolines [J].

Bora, Pranjal Protim ;

Luo, Zeng-Liang ;

Chen, Li ;

Kang, Qiang .

TETRAHEDRON, 2016, 72 (11) :1467-1471

[7] Enantioselective Synthesis of (+)-Petromyroxol, Enabled by Rhodium-Catalyzed Denitrogenation and Rearrangement of a 1-Sulfonyl-1,2,3-Triazole [J].

Boyer, Alistair .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (09) :4771-4775

[8] Transition-Metal-Catalyzed Denitrogenative Transannulation: Converting Triazoles into Other Heterocyclic Systems [J].

Chattopadhyay, Buddhadeb ;

Gevorgyan, Vladimir .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (04) :862-872

[9] Rh-Catalyzed Transannulation of N-Tosyl-1,2,3-Triazoles with Terminal Alkynes [J].

Chattopadhyay, Buddhadeb ;

Gevorgyan, Vladimir .

ORGANIC LETTERS, 2011, 13 (14) :3746-3749

[10] Total synthesis of (-)- and ent-(+)-vindoline [J].

Choi, YG ;

Ishikawa, H ;

Velcicky, J ;

Elliott, GI ;

Miller, MM ;

Boger, DL .

ORGANIC LETTERS, 2005, 7 (20) :4539-4542

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