Gold(I)-Catalyzed Oxidative Cascade Cyclization of 1,4-Diyn-3-ones for the Construction of Tropone-Fused Furan Scaffolds

被引：42

作者：

Hamada, Naoka ^{[1
]}

Yamaguchi, Ayuta ^{[1
]}

Inuki, Shinsuke ^{[1
]}

Oishi, Shinya ^{[1
]}

Ohno, Hiroaki ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 15期

关键词：

OXIDATION/1,2-ALKYNYL MIGRATION/CYCLIZATION CASCADE; GOLD CATALYSIS; POLYCYCLIC COMPOUNDS; EFFICIENT SYNTHESIS; ALKYNES; CYCLOAROMATIZATION; INSERTIONS; INHIBITORS; MIGRATION; CARBENES;

D O I：

10.1021/acs.orglett.8b01524

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Gold(I)-catalyzed cascade cyclization of 1,4-diyn-3-ones with a pyridine N-oxide enabled direct construction of a benzo[6,7]cyclohepta[1,2-b]furan scaffold with the formation of four bonds. This reaction would proceed through oxidative cyclization, alkynyl migration, and 5-endo-dig type cyclization. Synthesis of benzotropone-fused naphtho[1,2-b]furans through a two-step sequence, including epoxidation and In(OTf)(3)-catalyzed intramolecular carbon carbon bond formation, is also presented.

引用

页码：4401 / 4405

页数：5

共 41 条

[1] Gold-catalysed reactions of diynes
Asiri, Abdullah M.
Hashmi, A. Stephen K.
[J]. CHEMICAL SOCIETY REVIEWS, 2016, 45 (16) : 4471 - 4503
[2] Gold-Catalyzed Rearrangements: Reaction Pathways Using 1-Alkenyl-2-alkynylcyclopropane Substrates
Barluenga, Jose
Tudela, Eva
Vicente, Ruben
Ballesteros, Alfredo
Tomas, Miguel
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (09) : 2107 - 2110
[3] A Four-Step Total Synthesis of Radermachol
Buccini, Marco
Piggott, Matthew J.
[J]. ORGANIC LETTERS, 2014, 16 (09) : 2490 - 2493
[4] Design and synthesis of 2,3-dihydro- and 5-chloro-2,3-dihydro-naphtho-[1,2-b]furan-2-carboxylic acid N-(substitutedphenyl)amide analogs and their biological activities as inhibitors of NF-κB activity and anticancer agents
Choi, Minho
Jo, Hyeju
Kim, Dayoung
Yun, Jieun
Kang, Jong-Soon
Kim, Youngsoo
Jung, Jae-Kyung
Hong, Jin Tae
Cho, Jungsook
Kwak, Jae-Hwan
Lee, Heesoon
[J]. ARCHIVES OF PHARMACAL RESEARCH, 2016, 39 (05) : 618 - 630
[5] Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity
Dorel, Ruth
Echavarren, Antonio M.
[J]. CHEMICAL REVIEWS, 2015, 115 (17) : 9028 - 9072
[6] Gold and platinum catalysis-a convenient tool for generating molecular complexity
Fuerstner, Alois
[J]. CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) : 3208 - 3221
[7] Discovery of Novel CXCR2 Inhibitors Using Ligand-Based Pharmacophore Models
Ha, Helen
Debnath, Bikash
Odde, Srinivas
Bensman, Tim
Ho, Henry
Beringer, Paul M.
Neamati, Nouri
[J]. JOURNAL OF CHEMICAL INFORMATION AND MODELING, 2015, 55 (08) : 1720 - 1738
[8] Asymmetric rhodium-catalyzed hydrogenation meets gold-catalyzed cyclization: Enantioselective synthesis of 8-hydroxytetrahydroisoquinolines
Hashmi, A. Stephen K.
Haufe, Patrick
Schmid, Christoph
Nass, Andreas Rivas
Frey, Wolfgang
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (20) : 5376 - 5382
[9] Gold catalysis
Hashmi, A. Stephen K.
Hutchings, Graham J.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (47) : 7896 - 7936
[10] Homogeneous Gold Catalysis Beyond Assumptions and Proposals-Characterized Intermediates
Hashmi, A. Stephen K.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (31) : 5232 - 5241

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