Synthesis of pyrone-annulated 2-oxabicyclo[3.3.1]nonanes by palladium-catalyzed cyclization of 4-hydroxy-2-pyrones with allylic bisacetates

被引：2

作者：

Yoshida, Masahiro ^{[1
]}

Shibata, Miki ^{[2
]}

Mukae, Saaya ^{[1
]}

Kinoshita, Kouki ^{[2
]}

Matsumoto, Kenji ^{[1
]}

Hirokane, Tsukasa ^{[1
]}

机构：

[1] Tokushima Bunri Univ, Fac Pharmaceut Sci, Yamashiro Cho, Tokushima 7708514, Japan

[2] Tokushima Univ, Grad Sch Pharmaceut Sci, 1-78-1 Sho Machi, Tokushima 7708505, Japan

来源：

TETRAHEDRON LETTERS | 2019年 / 60卷 / 49期

基金：

日本学术振兴会;

关键词：

Palladium; Cyclization; pi-Allylpalladium; Pyrones; TANDEM ALLYLATION; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; HUPERZINE-A; ROUTE; 3-METHYLENE-1,2,3,4-TETRAHYDROPYRIDINES; 2-VINYL-2,3-DIHYDROPYRROLES; BICYCLOANNULATION; DERIVATIVES; ANALOGS;

D O I：

10.1016/j.tetlet.2019.151262

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclization of 4-hydroxy-2-pyrones with allylic bisacetates by a palladium catalyst is described. Pyrone-annulated 2-oxabicyclo[3.3.1]nonane derivatives were regioselectively produced from the reaction of 4-hydroxy-2-pyrones with 1,4-diacetoxy-2-cyclohexene at high temperature. The reaction would proceed via a migration of the pi-allylpalladium intermediate. (C) 2019 Elsevier Ltd. All rights reserved.

引用

页数：4

共 19 条

[1] Regio- and enantioselective synthesis of functionalized tetrahydroquinolines by palladium-catalyzed cyclization of 2-amidophenylmalonates with allylic bisacetates
Yoshida, Masahiro
Maeyama, Yohei
Shishido, Kozo
TETRAHEDRON, 2012, 68 (48) : 9962 - 9972
[2] Synthesis of functionalized 2-vinyl-2,3-dihydropyrroles and 3-methylene-1,2,3,4-tetrahydropyridines by palladium-catalyzed cyclization of β-enaminocarbonyl compounds with allylic bisacetates
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Namba, Kosuke
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (15) : 2394 - 2403
[3] Regiocontrolled Construction of Furo[3,2-c]pyran-4-one Derivatives by Palladium-Catalyzed Cyclization of Propargylic Carbonates with 4-Hydroxy-2-pyrones
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JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (04) : 1687 - 1692
[4] Palladium-Catalyzed [4+2] Cycloaddition of Hydroxy-Tethered Allylic Carbonates with Alkenes: Synthesis of Functionalized Tetrahydropyrans
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Shi, Wangyu
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SYNLETT, 2001, (12) : 1974 - 1976
[6] Generation of diverse 2-pyrones via palladium-catalyzed site-selective Suzuki-Miyaura couplings of 3-bromo-4-tosyloxy-2-pyrone
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Ding, Qiuping
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ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (18) : 6265 - 6270
[7] Synthesis of Azulenopyridinones through Palladium-Catalyzed Oxidative [4+2] Cyclization Reactions ofN-Methoxyazulene-1-and 2-carboxamides with Alkynes
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ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (21) : 4749 - 4754
[8] Synthesis of 2,3-Dihydroxyhex-4-enoates by Palladium-Catalyzed Allylic Alkylations of Carbohydrate Derived Vinyl Lactones
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SYNTHESIS-STUTTGART, 2008, (22): : 3682 - 3686
[9] Palladium-Catalyzed Intermolecular Aerobic Oxidative Cyclization of 2-Ethynylanilines with Isocyanides: Regioselective Synthesis of 4-Halo-2-aminoquinolines
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JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (20) : 10319 - 10328
[10] Palladium-Catalyzed Intramolecular Cyclization of 2-Iodobenzamides: An Efficient Synthesis of 3-Acyl Isoindolin-1-ones and 3-Hydroxy-3-acylisoindolin-1-ones
Chen, Wanli
Jin, Lina
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Mo, Weimin
SYNLETT, 2013, 24 (14) : 1856 - 1860

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