Molecular Diversity of Tonghaosu Analogues, Selective Oxidation of the exo-Cyclic Double Bond of Spiroacetal Enol Ethers and Diasteroselective Synthesis of Spiro-Pyranone

Biaolin Yin; Jinqiang Lai; Zeren Zhang; Yulin Wu

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Molecular Diversity of Tonghaosu Analogues, Selective Oxidation of the exo-Cyclic Double Bond of Spiroacetal Enol Ethers and Diasteroselective Synthesis of Spiro-Pyranone

机译：Tonghaosu类似物的分子多样性，螺缩醛烯醇醚的环外双键选择性氧化和螺吡喃酮的非对映选择性合成

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摘要

Two methods including NBS/AgNO₃ system and MCPBA oxidation have been developed for the selective oxidations of the exo-cyclic double bond of spiroacetal enol ethers 2 with multi reactive sites into spiro-pyanones 3 and 4. In addition, possible mechanisms for these conversions are proposed.

机译：已经开发出两种方法，包括NBS / AgNO _{3 系统和MCPBA氧化，用于将具有多个反应位点的螺缩醛烯醇醚2的环外双键选择性氧化为螺吡喃酮3和4。此外，提出了这些转换的可能机制。}

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来源
《Chinese Journal of Chemistry》 |2010年第12期|p.2335-2338|共4页
作者
Biaolin Yin; Jinqiang Lai; Zeren Zhang; Yulin Wu;
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作者单位

School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, Guangdong 510640, China;

Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou, Zhejiang 310012, China;

State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China;

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原文格式 PDF
正文语种 eng
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关键词
spiroacetal; enol ether; oxidation; diasteroselectivity;

机译：螺缩醛;烯醇醚;氧化;非对映选择性;

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1. Molecular Diversity of Tonghaosu Analogues, Selective Oxidation of the exo-Cyclic Double Bond of Spiroacetal Enol Ethers and Diasteroselective Synthesis of Spiro-Pyranone [J] . Yin Biaolin, Lai Jinqiang, Zhang Zeren, 中国化学（英文版） . 2010,第012期
2. Molecular diversity from Tonghaosu analogues, selective reduction of the endo-cyclic double bond of tonghaosu analogues and the synthesis of cyclopentenone derivatives [J] . Yin BL., Fan JF., Gao Y., Synlett . 2003,第3期

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3. SYNTHESIS OF SPIROACETAL ENOL ETHERS VIA INTRAMOLECULAR CONJUGATE ADDITION OF HEMIACETAL ALKOXIDES TO ALKYNOATES [J] . Toshima H., Inamura S., Ichihara A., Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 1996,第32期

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5. Total Synthesis of Anthraquinone–Xanthone Natural Products and Intermolecular Alkenylation of Silyl Enol Ethers [D] . Holmbo, Stephen Daniel. 2019

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6. Ni-Catalyzed Intramolecular C–O Bond Formation: Synthesis of Cyclic Enol Ethers [O] . Seo-Jung Han, Ryohei Doi, Prof. Dr. Brian M. Stoltz -1

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7. Oxidative Carbon-Carbon Bond Formation via Silyl Bis-enol Ethers: Controlled Cross-Coupling for the Synthesis of Quaternary Centers [O] . -1

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Molecular Diversity of Tonghaosu Analogues, Selective Oxidation of the exo-Cyclic Double Bond of Spiroacetal Enol Ethers and Diasteroselective Synthesis of Spiro-Pyranone

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