Dehalogenation of 1,3‐Diiodotricyclo[3.3.0.0<sup>3,7</sup>]octane: Generation of 1,3‐Dehydrotricyclo[3.3.0.0<sup>3,7</sup>]octane, a 2,5‐Methano‐Bridged [2.2.1]Propellane

Ayats, Carles; Camps, Pelayo; Fernández, José A.; Vázquez, Santiago

doi:10.1002/chem.200600859

Cited by 6 publications

References 45 publications

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The McMurry Coupling and Related Reactions

Takeda

Tsubouchi

2013

Organic Reactions

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The McMurry coupling reaction has been recognized as one of the most efficient methods for the synthesis of alkenes from carbonyl compounds. This reaction can be applied to the preparation of various alkenes that are otherwise difficult to prepare. For example, sterically congested tetrasubstituted alkenes as well as medium to large membered rings involving natural products may be accessed via this process. This coupling utilizes various low‐valent titanium reagents generated by the reduction of titanium (III or IV) chloride with K, Zn, LiAlH 4 , C 8 K, amongst others. Furthermore, a variety of low‐valent metal species other than titanium, including aluminum, zirconium, niobium, molybdenum, indium, tungsten, and samarium, have also been found to promote the reductive coupling of carbonyl compounds. The scope and limitations of these reagent systems are reviewed in this chapter, together with the stereochemistry and reaction mechanism. This reaction is categorized into four coupling modes: i) homocoupling giving symmetrical alkenes, ii) mixed coupling giving unsymmetrical alkenes, iii) intramolecular coupling giving cycloalkenes, and iv) tandem coupling giving cyclic polyenes. Characteristics of these reaction modes are described briefly. A selection of synthetic applications are reviewed, including examples of the preparation of sterically congested and strained alkenes, medium to large‐ring compounds, biologically active targets, as well as substrates applicable in material science. Experimental conditions used for this versatile process are summarized to assist the choice of suitable conditions.

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The McMurry Coupling and Related Reactions

Takeda

Tsubouchi

2013

Organic Reactions

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Polycyclic N‐Benzamido Imides with Potent Activity against Vaccinia Virus

et al. 2010

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The synthesis and antiviral activity of a series of novel polycyclic analogues of the orthopoxvirus egress inhibitor tecovirimat (ST-246) is presented. Several of these compounds display sub-micromolar activity against vaccinia virus, and were more potent than cidofovir (CDV). The more active compounds were about 10-fold more active than CDV, with minimum cytotoxic concentrations above 100 μM. Chemical manipulations of the two carbon-carbon double bonds present in the compounds were carried out to further explore the structure-activity relationships of these new polycyclic imides. Hydrogenation of the two carbon-carbon double bonds decreases antiviral activity, whereas either cyclopropanation or epoxidation of the double bonds fully eliminates the antiviral activity.

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Double Methylenecyclopentane Annulation of Succinimides: Easy Access to 3,7‐Dioxobicyclo[3.3.0]octane‐1,5‐dicarboximides

et al. 2009

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Keywords: Alkylation / Annulation / Carbocycles / Lithiation / Ozonolysis N-Alkylsuccinimides reacted with excess of LHMDS and 3-chloro-2-(chloromethyl)-1-propene to give in medium yields N-alkyl-3,7-dimethylenebicyclo[3.3.0]octane-1,5-dicarboximides, which were ozonized to the corresponding 3,7-dioxobicyclo[3.3.0]octane-1,5-dicarboximides. When these alkylations were carried out by using LDA as the base, cis-N-

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Dehalogenation of 1,3‐Diiodotricyclo[3.3.0.0^3,7]octane: Generation of 1,3‐Dehydrotricyclo[3.3.0.0^3,7]octane, a 2,5‐Methano‐Bridged [2.2.1]Propellane

Cited by 6 publications

References 45 publications

The McMurry Coupling and Related Reactions

The McMurry Coupling and Related Reactions

Polycyclic N‐Benzamido Imides with Potent Activity against Vaccinia Virus

Double Methylenecyclopentane Annulation of Succinimides: Easy Access to 3,7‐Dioxobicyclo[3.3.0]octane‐1,5‐dicarboximides

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Dehalogenation of 1,3‐Diiodotricyclo[3.3.0.03,7]octane: Generation of 1,3‐Dehydrotricyclo[3.3.0.03,7]octane, a 2,5‐Methano‐Bridged [2.2.1]Propellane

Cited by 6 publications

References 45 publications

The McMurry Coupling and Related Reactions

The McMurry Coupling and Related Reactions

Polycyclic N‐Benzamido Imides with Potent Activity against Vaccinia Virus

Double Methylenecyclopentane Annulation of Succinimides: Easy Access to 3,7‐Dioxobicyclo[3.3.0]octane‐1,5‐dicarboximides

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Product

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Dehalogenation of 1,3‐Diiodotricyclo[3.3.0.0^3,7]octane: Generation of 1,3‐Dehydrotricyclo[3.3.0.0^3,7]octane, a 2,5‐Methano‐Bridged [2.2.1]Propellane