Tandem 5-Exo-dig-5-exo-trig Radical Cyclization leading to a 6,5-Ring Fused Carbobicycle possessing Two Contiguous Quaternary Carbons at the Bridgehead and its Adjacent Positions

Nagano, Hajime; Ohtani, Yohko; Odake, Eiko; Nakagawa, Junko; Mori, Yusuke; Yajima, Tomoko

doi:10.1039/a900444k

Cited by 4 publications

(2 citation statements)

References 12 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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show abstract

“…In recent years, this type of molecular structure has been studied as an attractive synthetic target. The known synthetic methods to construct such spiro compounds involve Diels−Alder reactions of α-methylene lactone, radical cyclization of bromo alkene or alkyne, ring-closing metathesis reaction of diallyl oxolane derivatives, lactonization of chloro sulfinyl carboxylate, and metal-catalyzed insertion reaction of diazo compounds . However, to date, there are only a few reports of the synthesis of substituted 2-oxaspirocyclic derivatives with quaternary carbon centers due to demanding control of stereoselectivity.…”

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confidence: 99%