Studies on electrocyclization in bicyclo[4.4.1]undeca-2,4-diene and bicyclo[4.2.1]nona-2,4-diene systems

Rigby, James H.; Claire, V. De Sainte; Heeg, Mary Jane

doi:10.1016/0040-4039(96)00328-0

Cited by 9 publications

(2 citation statements)

References 8 publications

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“…Rigby and co‐workers studied the 4‐π‐photocyclization of a series of complex bicyclic cycloheptadienes. For example, dienes 71 and 73 underwent stereoselective photocyclization upon irradiation, furnishing the corresponding cyclobutene products ( 72 and 74 ) respectively in high yields (Scheme ) . It was also demonstrated that the cyclobutene in 72 could be cleaved through ozonolysis, giving the corresponding diol after reduction.…”

Section: Carbocyclic 13‐diene Systemsmentioning

confidence: 99%

4‐π‐Photocyclization: Scope and Synthetic Applications

Coote

2019

Eur J Org Chem

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This minireview highlights the scope of 4‐π‐photocyclizations (photoinduced electrocyclizations that involve 4 pi electrons and generate bicyclic cyclobutenes from 1,3‐dienes), including an overview of the historical progressions as well as recent developments. A range of 1,3‐diene substrates is covered, including cycloheptatrienes, tropones, tropolones, cyclic 1,3‐dienes, 2‐pyrones, 2‐pyridones, pyrimidines, 1,2‐dihydropyridines, and 1,2‐dihydro‐pyridazines. The bicyclic cyclobutene products formed through the photocyclizations are highly versatile synthetic intermediates, and examples of the application of these building blocks in the context of synthetic methodology development, natural product synthesis, medicinal chemistry and materials chemistry are featured throughout.

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Section: Carbocyclic 13‐diene Systemsmentioning

confidence: 99%

4‐π‐Photocyclization: Scope and Synthetic Applications

Coote

2019

Eur J Org Chem

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“…Scheme outlines our initial retrosynthetic analysis of salvileucalin C ( 1 ). We rationalized that 1 might be synthesized from salvileucalin D ( 2 ) through cyclobutene formation by a photoinduced 4π-electrocyclic ring closure, while the latter could be derived from a 6π-electrocyclic ring-opening reaction of a benzonorcaradiene moiety of salvipuberulin ( 3 ) followed by [1,5]-sigmatropic hydrogen migration . For the construction of 3 , we envisaged a radical initiated Beckwith–Dowd ring expansion to forge the [5,6]-bicyclic framework of the molecule.…”

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confidence: 99%

Diastereoselective Total Synthesis of Salvileucalin C

Zhang

Xuan

et al. 2014

Org. Lett.

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A concise and efficient approach for the diastereoselective total synthesis of salvileucalin C, as well as their biosynthetically related diterpenoids salvileucalin D, salvipuberulin, isosalvipuberulin, and dugesin B, has been reported for the first time. The key features of the strategy are based on a Beckwith-Dowd ring expansion, a tandem diastereoselective Stille coupling/debromination/desilylation/lactonization reaction, and a photoinduced electrocyclic ring contraction.

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7α‐Acetoxy‐(1Hβ, 6Hβ)‐Bicyclo[4.4.1]Undeca‐2,4,8‐Triene via Chromium‐Mediated Higher Order Cycloaddition

Rigby

Fales

2003

Organic Syntheses

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7α‐acetoxy‐(1Hβ, 6Hβ)‐bicyclo[4.4.1]undeca‐2,4,8‐triene via chromium‐mediated higher order cycloaddition intermediate: tricarbonyl(η 6 ‐cycloheptatriene)chromium(0) product: ∼98% pure, 7α‐acetoxy‐(1Hβ, 6Hβ)‐bicyclo[4.4.1]undeca‐2,4,8‐triene reactant: (E)‐1‐acetoxy‐1,3‐butadiene byproduct: [6π + 2π] cycloadduct

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Studies on electrocyclization in bicyclo[4.4.1]undeca-2,4-diene and bicyclo[4.2.1]nona-2,4-diene systems

Cited by 9 publications

References 8 publications

4‐π‐Photocyclization: Scope and Synthetic Applications

4‐π‐Photocyclization: Scope and Synthetic Applications

Diastereoselective Total Synthesis of Salvileucalin C

7α‐Acetoxy‐(1Hβ, 6Hβ)‐Bicyclo[4.4.1]Undeca‐2,4,8‐Triene via Chromium‐Mediated Higher Order Cycloaddition

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