Kinetically controlled ring-closing metathesis: Synthesis of a potential scaffold for 12-membered salicylic macrolides

Matsuya Y; Takayanagi S; Nemoto H

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Kinetically controlled ring-closing metathesis: Synthesis of a potential scaffold for 12-membered salicylic macrolides

机译：动力学控制的闭环易位：合成十二元水杨酸内酯的潜在支架。

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For the synthesis of a 12-membered salicylic macrolide scaffold, ring-closing metathesis (RCM) of a omega-diene compound was planned. The stereochemical outcome of the RCM reaction changed depending on the type of Ru catalyst that was used; a "first-generation" Grubbs catalyst produced exclusively the E isomer and "second-generation" catalysts provided a mixture of the E and Z isomers under kinetic control (not thermodynamic control). Considerations for the E/Z selectivity are described.

机译：为了合成12元水杨酸大环内酯骨架，计划了ω-二烯化合物的闭环易位（RCM）。 RCM反应的立体化学结果根据所用Ru催化剂的类型而有所不同。 “第一代” Grubbs催化剂仅生产E异构体，“第二代”催化剂在动力学控制（不是热力学控制）下提供E和Z异构体的混合物。描述了E / Z选择性的注意事项。

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《Chemistry: A European journal》 |2008年第17期|共7页
作者
Matsuya Y; Takayanagi S; Nemoto H;
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正文语种 eng
中图分类化学;
关键词
catalysis; macrocycles; metathesis; ruthenium; selectivity; FORMAL TOTAL-SYNTHESIS; CATALYZED OLEFIN METATHESIS; RUTHENIUM CARBENE COMPLEXES; DENSELY FUNCTIONALIZED DIENE; THEORETICAL PERSPECTIVE; SALICYLIHALAMIDE-A; MACROSPHELIDE-B; OXIMIDINE-II; MECHANISM; MACROCYCLIZATION;

机译：催化;大环化合物;复分解;钌;选择性;正式合成;催化烯烃复分解;钌碳络合物;稠密功能二烯;理论观点;水杨酰胺-甲酰胺;大环磷酰胺;环氧化物;

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1. Kinetically controlled ring-closing metathesis: Synthesis of a potential scaffold for 12-membered salicylic macrolides [J] . Matsuya Y, Takayanagi S, Nemoto H Chemistry: A European journal . 2008,第17期

机译：动力学控制的闭环易位：合成十二元水杨酸内酯的潜在支架。
2. A Formal Total Synthesis of Eleutherobin Using the Ring-Closing Metathesis (RCM) Reaction of a Densely Functionalized Diene as the Key Step: Investigation of the Unusual Kinetically Controlled RCM Stereochemistry [J] . Damiano Castoldi, Laura Panigada, Ofer Sharon, Chemistry: A European journal . 2006,第1期

机译：以致密功能化的二烯的闭环置换（RCM）反应为关键步骤的全合成大黄素：异常动力学控制的RCM立体化学研究
3. A formal total synthesis of eleutherobin using the ring-closing metathesis (RCM) reaction of a densely functionalized diene as the key step: Investigation of the unusual kinetically controlled RCM stereochemistry [J] . Castoldi D, Caggiano L, Panigada L, Chemistry: A European journal . 2005,第1期

机译：使用致密功能化的二烯的开环复分解（RCM）反应作为关键步骤，正式合成eleutherobin，这一关键步骤是：研究异常的动力学控制的RCM立体化学
4. Parallel Solid-Phase Synthesis of Macrocyclic Peptidomimetics Using Ru-Catalyzed Ring-Closing Metathesis and a New Application of Cross Metathesis [C] . Sylvie Beaubien, Hamid R. Hoveyda, Martin Vezina American Peptide Symposium . 2009

机译：用Ru催化的闭环复分解和交叉复分解的新应用，平行固相合成大环肽肽剂及新应用
5. Total synthesis of brevenal; synthesis of the AB- and E-ring subunits of brevenal and studies of olefinic-lactone ring-closing metathesis using a reduced titanium alkylidene; synthesis of (R)-(-)-muscone and (R)-(+)-muscopyridine [D] . Rohanna, John C. 2011

机译：全合成brevenal；合成brevenal的AB-和E-环亚基，并使用还原的亚烷基钛研究烯烃-内酯闭环复分解；（R）-（-）-muscone和（R）-（+）-muscopyridine的合成
6. Synthesis of macrocyclic natural products by catalyst-controlled stereoselective ring-closing metathesis [O] . Miao Yu, Chenbo Wang, Andrew F. Kyle, -1

机译：通过催化剂控制立体选择性闭环复分解的大环的天然产物的合成
7. Stereoselective Synthesis of the Phorboxazole A Macrolide by Ring-Closing Metathesis [O] . -1

机译：通过环闭复分解的立体选择性合成富罗拉唑的大环内酯

Kinetically controlled ring-closing metathesis: Synthesis of a potential scaffold for 12-membered salicylic macrolides

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