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

被引：59

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
Adams, DJ
Blake, AJ
Cooke, PA
Gill, CD
Simpkins, NS
[J]. TETRAHEDRON, 2002, 58 (23) : 4603 - 4615
[2] Enantioselective organocatalytic construction of pyrroloindolines by a cascade addition-cyclization strategy: Synthesis of (-)-flustramine B
Austin, JF
Kim, SG
Sinz, CJ
Xiao, WJ
MacMillan, DWC
[J]. 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
Avendano, Carmen
Caballero, Esmeralda
Mendez-Vidal, Cristina
de Quesada, Ana R.
Carlos Menendez, J.
[J]. LETTERS IN DRUG DESIGN & DISCOVERY, 2006, 3 (06) : 369 - 377
[4] Synthesis of strychnine
Bonjoch, J
Solé, D
[J]. 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
Boonsombat, Jutatip
Zhang, Hongjun
Chughtai, Majid J.
Hartung, John
Padwa, Albert
[J]. 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
Bora, Pranjal Protim
Luo, Zeng-Liang
Chen, Li
Kang, Qiang
[J]. 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
Boyer, Alistair
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (09) : 4771 - 4775
[8] Transition-Metal-Catalyzed Denitrogenative Transannulation: Converting Triazoles into Other Heterocyclic Systems
Chattopadhyay, Buddhadeb
Gevorgyan, Vladimir
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (04) : 862 - 872
[9] Rh-Catalyzed Transannulation of N-Tosyl-1,2,3-Triazoles with Terminal Alkynes
Chattopadhyay, Buddhadeb
Gevorgyan, Vladimir
[J]. ORGANIC LETTERS, 2011, 13 (14) : 3746 - 3749
[10] Total synthesis of (-)- and ent-(+)-vindoline
Choi, YG
Ishikawa, H
Velcicky, J
Elliott, GI
Miller, MM
Boger, DL
[J]. ORGANIC LETTERS, 2005, 7 (20) : 4539 - 4542

← 1 2 3 4 5 6 →