Co_2(CO)_8-mediated Endo Mode Cyclization of Epoxy-alcohol: Synthesis of 2-Ethynyl-3-hydroxy-2-methyltetrahydropyran and 2-Ethynyl-3-hydroxy-3-methyltetrahydropyran Derivatives

Chisato Mukai; Sumie Yamaguchi; In Jong Kim; Miyoji Hanaoka

首页> 外文期刊>Chemical and Pharmaceutical Bulletin >Co_2(CO)_8-mediated Endo Mode Cyclization of Epoxy-alcohol: Synthesis of 2-Ethynyl-3-hydroxy-2-methyltetrahydropyran and 2-Ethynyl-3-hydroxy-3-methyltetrahydropyran Derivatives

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Co_2(CO)_8-mediated Endo Mode Cyclization of Epoxy-alcohol: Synthesis of 2-Ethynyl-3-hydroxy-2-methyltetrahydropyran and 2-Ethynyl-3-hydroxy-3-methyltetrahydropyran Derivatives

机译：Co_2（CO）_8介导的环氧醇的内模环化：2-乙炔基-3-羟基-2-甲基四氢吡喃和2-乙炔基-3-羟基-3-甲基四氢吡喃衍生物的合成

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Successive treatment of 4,5-epoxy-5-methyl-7-trimethylsilyl-6-heptyne-1-ol with Co_2(CO)_8 at 0 ℃ and a catalytic amount of BF_3·OEt_2 at -78 ℃ gave the tetrahydropyran derivatives with the cobalt-complexed moiety. Similarly 4,5-epoxy-4-methyl-7-trimethylsilyl-6-heptyne-1-ol underwent ring closure under the above conditions to provide the corresponding tetrahydropyran derivatives. The preferential endo mode cyclization over the exo one was observed in these experiments.

机译：在0℃下连续处理4,5-环氧--5-甲基-7-三甲基甲硅烷基-6-庚炔-1-醇，并在-78℃催化量BF_3·OEt_2，得到四氢吡喃衍生物。钴络合物部分。类似地，在上述条件下将4，5-环氧-4-甲基-7-三甲基甲硅烷基-6-庚炔-1-醇进行闭环以提供相应的四氢吡喃衍生物。在这些实验中观察到了优先于外型的内模环化。

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来源
《Chemical and Pharmaceutical Bulletin》 |2001年第5期|共6页
作者
Chisato Mukai; Sumie Yamaguchi; In Jong Kim; Miyoji Hanaoka;
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正文语种 eng
中图分类药学;化学;
关键词
endo mode cyclization; cobalt complex; tetrahydropyran ring; epoxy alkyne;

机译：内模环化;钴配合物;四氢吡喃环;环氧炔烃;

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1. Co_2(CO)_8-mediated Endo Mode Cyclization of Epoxy-alcohol: Synthesis of 2-Ethynyl-3-hydroxy-2-methyltetrahydropyran and 2-Ethynyl-3-hydroxy-3-methyltetrahydropyran Derivatives [J] . Chisato Mukai, Sumie Yamaguchi, In Jong Kim, Chemical and Pharmaceutical Bulletin . 2001,第5期

机译：Co_2（CO）_8介导的环氧醇的内模环化：2-乙炔基-3-羟基-2-甲基四氢吡喃和2-乙炔基-3-羟基-3-甲基四氢吡喃衍生物的合成
2. Co2(CO)8-mediated endo mode cyclization of epoxy-alcohol: synthesis of 2-ethynyl-3-hydroxy-2-methyltetrahydropyran and 2-ethynyl-3-hydroxy-3-methyltetrahydropyran derivatives. [J] . Mukai C, Yamaguchi S, Kim IJ, Chemical and Pharmaceutical Bulletin . 2001,第5期

机译：Co 2（CO）8介导的环氧-醇的内模环化：2-乙炔基-3-羟基-2-甲基四氢吡喃和2-乙炔基-3-羟基-3-甲基四氢吡喃衍生物的合成。
3. A new entry to carbocycles: synthesis of cyclopentene and cyclohexene derivatives through endo-mode ring closure of allenyl sulfones [J] . Chisato Mukai, Rie Ukon, Norikazu Kuroda Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2003,第8期

机译：碳环化合物的新进入途径：通过烯基砜的内模闭环合成环戊烯和环己烯衍生物
4. Synthesis and Anti-inflammatory Activity of 3-Aryloxylindolizine Derivatives via Sonogashira Coupling/5-endo-ting Cycloisomerization Domino Strategy [C] . Yong Wei, Chengqiao Cao, Jianfeng Chen, International Conference on Chemical Engineering and Advanced Materials . 2013

机译：通过Sonogashira偶联/ 5- endo-ting环偶化Domino策略的合成和抗炎活性。
5. New developments toward the synthesis of heterocycles and applications in green chemistry. I. A simple and essentially one-pot synthesis of N-aminated heterocycles using phase transfer catalyst (Aliquat-336). II. Synthesis of pharmaceutically important pyrrole derivatives. III. Applications in green chemistry: Surfactant-mediated environmentally friendly cleavage of aromatic esters and trans-esterification under solvent-free neutral conditions . [D] . Patel, Nitinchandra. 2005

机译：杂环合成的新进展及其在绿色化学中的应用。 I.使用相转移催化剂（Aliquat-336）简单且基本上一锅合成N-胺化的杂环。二。药学上重要的吡咯衍生物的合成。三，在绿色化学中的应用：在无溶剂的中性条件下，表面活性剂介导的环境友好的芳族酯裂解和酯交换反应。
6. Synthesis and Transformations of di-endo-3-Aminobicyclo-2.2.2oct-5-ene-2-carboxylic Acid Derivatives [O] . Márta Palkó, Pál Sohár, Ferenc Fülöp 2011

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7. Oligosiloles: First Synthesis Based on a Novel Endo-Endo Mode Intramolecular Reductive Cyclization of Diethynylsilanes (SYNTHETIC ORGANIC CHEMISTRY - Synthetic Design) [O] . Tamao Kohei, Yamaguchi Shigehiro 1995

机译：Oligosiloles：基于二乙炔基硅烷的新型内-内-端模式分子内还原环化的首次合成（合成有机化学-合成设计）
8. Synthesis of a 2-Oxabrendane Derivative via Reaction of endo-5-Acetyl-7,7-dimethoxynorborn-2-ene with N-Bromosuccinimide [R] . Watson, W. H., Kashyap, R. P., Marchand, A. P., 1991

机译：内-5-乙酰基-7,7-二甲氧基降冰片烯-2-烯与N-溴代琥珀酰亚胺反应合成2-氧杂戊二烯衍生物

Co_2(CO)_8-mediated Endo Mode Cyclization of Epoxy-alcohol: Synthesis of 2-Ethynyl-3-hydroxy-2-methyltetrahydropyran and 2-Ethynyl-3-hydroxy-3-methyltetrahydropyran Derivatives

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