Formal Synthesis of (+)-Laurencin by Gold(I)-Catalyzed Intramolecular Dehydrative Alkoxylation

Megan L. Lanier; Hyeri Park; Paramita Mukherjee; Jacob C. Timmerman; Anthony A. Ribeiro; Ross A. Widenhoefer; Jiyong Hong

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Formal Synthesis of (+)-Laurencin by Gold(I)-Catalyzed Intramolecular Dehydrative Alkoxylation

机译：（+） - 黄金（I） - 催化分子内脱水烷氧基化的正式合成 - Laurencin

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摘要

8-Membered cyclic ethers are found in a wide range of natural products; however, they are challenging synthetic targets due to enthalpic and entropic barriers. The gold(I)-catalyzed intramolecular dehydrative alkoxylation of ω-hydroxy allylic alcohols was explored to stereoselectively construct α,α’-cis-oxocenes and further applied in a formal synthesis of (+)-laurencin. The gold(I)-catalyzed intramolecular dehydrative alkoxylation may constitute an alternative method for the synthesis of molecular building blocks and natural products that contain highly functionalized 8-membered cyclic ethers.

机译：在各种天然产品中发现了8元环醚; 然而，由于焓和熵屏障，它们是挑战的合成目标。金（I） - 催化ω-羟基烯丙基醇的催化分子内脱水烷氧基化，以立体选择性构建α，α'-CIS-杂种糖，并进一步应用于（+） - Laurencin的正式合成。金（I） - 催化分子内脱水烷氧基化可以构成用于合成分子结构块和含有高官能化8-元环醚的天然产物的替代方法。

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《Chemistry: A European journal》 |2017年第30期|共5页
作者
Megan L. Lanier; Hyeri Park; Paramita Mukherjee; Jacob C. Timmerman; Anthony A. Ribeiro; Ross A. Widenhoefer; Jiyong Hong;
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作者单位

Department of Chemistry Duke University Durham North Carolina 27708 (USA);

Department of Chemistry Duke University Durham North Carolina 27708 (USA);

Department of Chemistry Duke University Durham North Carolina 27708 (USA);

Department of Chemistry Duke University Durham North Carolina 27708 (USA);

Duke University NMR Center and Department of Radiology Duke University Durham North Carolina 27710 (USA);

Department of Chemistry Duke University Durham North Carolina 27708 (USA);

Department of Chemistry Duke University Durham North Carolina 27708 (USA);

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原文格式 PDF
正文语种 eng
中图分类应用化学;
关键词
dehydrative alkoxylation; gold catalysis; whydroxy allylic alcohols; (+)-laurencin; natural products;

机译：脱水烷氧基化;金催化;Whydroxy烯丙基醇;（+） - Laurencin;天然产品;

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1. Formal Synthesis of (+)-Laurencin by Gold(I)-Catalyzed Intramolecular Dehydrative Alkoxylation [J] . Megan L. Lanier, Hyeri Park, Paramita Mukherjee, Chemistry: A European journal . 2017,第30期

机译：（+） - 黄金（I） - 催化分子内脱水烷氧基化的正式合成 - Laurencin
2. O-Heterocycle Synthesis via Intramolecular C-H Alkoxylation Catalyzed by Iron Acetylacetonate [J] . Yuyang Dong, Alexandra T. Wrobel, Gerard J. Porter, Journal of the American Chemical Society . 2021,第19期

机译：O-杂环通过铁乙酰丙酮催化催化的分子内C-H烷氧基化合成
3. Copper-Catalyzed Intramolecular C-H Alkoxylation of Diaryltriazoles: Synthesis of Tricyclic Triazole Benzoxazines [J] . Ma Xinyuan, Li Haotian, Xin Hong, Organic letters . 2020,第14期

机译：二芳基三唑的铜催化分子内C-H烷氧基化：三环三唑苯并恶嗪的合成
4. Negative resists for electron-beam lithography utilizing acid-catalyzed intramolecular dehydration of phenylcarbinol [C] . Sonoko Migitaka, Hitachi, Ltd., Advances in Resist Technology and Processing XIII . 1996

机译：利用苯甲醇的酸催化分子内脱水进行电子束光刻的负性抗蚀剂
5. 1. Axially-chiral 7-membered N-heterocyclic carbenes: Synthesis and application to palladium-catalyzed intramolecular aerobic oxidation of olefins 2. Development of palladium-catalyzed aerobic oxidative olefin amination reactions [D] . Scarborough, Christopher C. 2008

机译：1.轴向手性7元N-杂环卡宾：烯烃的钯催化分子内需氧氧化的合成及应用2.钯催化需氧氧化烯烃胺化反应的发展
6. Formal Synthesis of (+)-Laurencin via a Gold(I)-Catalyzed Intramolecular Dehydrative Alkoxylation [O] . Megan L. Lanier, Hyeri Park, Paramita Mukherjee, -1

机译：通过金（I）催化的分子内脱水烷氧基化的（+）-Laurencin的形式合成。
7. OHeterocycle Synthesis via Intramolecular CH Alkoxylation Catalyzed by Iron Acetylacetonate [O] . -1

机译：OHERERICYCLE通过铁乙酰丙酮催化催化的分细分CH烷氧基化合成

Formal Synthesis of (+)-Laurencin by Gold(I)-Catalyzed Intramolecular Dehydrative Alkoxylation

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