An expeditious approach to the synthesis of Angular Triquinane

Yadav, J. S.; Kumar, T. Kiran; Gadgil, V. R.

doi:10.1016/s0040-4039(00)92537-1

Cited by 16 publications

(2 citation statements)

References 17 publications

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“…10,204,205 The development of reaction sequences starting with a haloacetal cyclization has been actively investigated. 102,107,[206][207][208][209] An interesting deoxygenative cy- The last radical cyclization onto an aldehyde group is followed by trapping of the alkoxyl radical by triphenylphosphine, leading, after elimination of the phosphine oxide, to the deoxygenated product.…”

Section: Polycyclic Systems Via Cascade Cyclizationsmentioning

confidence: 99%

Radical Cyclization of Haloacetals: The Ueno-Stork Reaction

Salom‐Roig¹,

Dénès²,

Renaud³

2004

Synthesis

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The formation of the C-C bond using radical cyclization of haloacetals (Ueno-Stork reaction) has proven to be an extremely efficient method to access g-lactones and related compounds. This reaction is also highly attractive for the regio-and stereoselective introduction of side chains to cyclic and acyclic allylic alcohols. It has been used as a key step in many natural product syntheses and has proven to be particularly efficient for the stereoselective generation of quaternary carbon centers. This review focuses on the different methods available to carry out this radical cyclization, as well as on the stereochemical aspect of the reaction and its applications in total synthesis.

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Section: Polycyclic Systems Via Cascade Cyclizationsmentioning

confidence: 99%

Radical Cyclization of Haloacetals: The Ueno-Stork Reaction

Salom‐Roig¹,

Dénès²,

Renaud³

2004

Synthesis

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“…Other groups have used a similar strategy to provide a stereoselective access to angular triquinanes. Thus, Yadav applied the Stork and Ueno methods of radical cyclization of bromoacetals for the synthesis of the triquinane moiety. When the bromoacetal unit was present on a cyclopentene ring, in an α position relative to the double bond, the derived radical readily cyclized.…”

Section: The Radical Cyclization Approachmentioning

confidence: 99%

Selective Preparation of Complex Polycyclic Molecules from Acyclic Precursors via Radical Mediated- or Transition Metal-Catalyzed Cascade Reactions

Malacrìa

1996

Chem. Rev.

417

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Radical Cyclization Reactions

et al. 1996

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Radical cyclization reactions are among the most powerful and versatile methods for the construction of mono‐ and polycyclic systems. The advantages these reactions offer to the synthetic organic chemist include high functional group tolerance and mild reaction conditions combined with high levels of regio‐ and stereochemistry. Furthermore, the recent progress in radical chemistry has led to the development of a broad range of very useful practical methods to conduct radical cyclization reactions. In general, radical cyclization reactions comprise three basic steps: selective radical generation, radical cyclization, and conversion of the cyclized radical to the product. For the generation of the initial radical a broad variety of suitable precursors can be employed, such as halides, thio‐ and selenoethers, alcohols, aldehydes and hydrocarbons. The cyclization step usually involves the intramolecular addition of a radical to a multiple bond. Most often carbon–carbon multiple bonds are employed; however, there are also examples known for the addition to carbon–oxygen and carbon–nitrogen bonds. Depending on the method employed, the cyclized radical is converted to the desired product by trapping with a radical scavenger, by a fragmentation reaction, or by an electron transfer reaction. The section Mechanism, Regio‐ and Stereochemistry provides an introduction to the key features of radical cyclization with a special emphasis on the factors controlling the regio‐ and stereochemistry. The section Scope and Limitations covers the different methods used to conduct radical cyclization. The basic principles of radical chemistry and general practical considerations when conducting radical cyclizations are not discussed in detail. Several excellent review articles and books dealing with these topics are available.

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An expeditious approach to the synthesis of Angular Triquinane

Cited by 16 publications

References 17 publications

Radical Cyclization of Haloacetals: The Ueno-Stork Reaction

Radical Cyclization of Haloacetals: The Ueno-Stork Reaction

Selective Preparation of Complex Polycyclic Molecules from Acyclic Precursors via Radical Mediated- or Transition Metal-Catalyzed Cascade Reactions

Radical Cyclization Reactions

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