Synthesis and reactions of two stereoisomeric [4.5.5.5]fenestranes with bridgehead substituents

Weyermann, Philipp; Keese, Reinhart

doi:10.1016/j.tet.2011.03.086

Cited by 8 publications

(1 citation statement)

References 13 publications

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“…The synthesis of various fenestranes was accomplished in the Keese group − by employing appropriately substituted bicyclo[3.3.0]octenones as photocycloaddition precursors. The diastereoselectivity [e.g., in the transformation rac - 160 → rac - 161 (Scheme )] was high as the rigid bicyclic ring system forces the tether to approach the enone from one diastereotopic face.…”

Section: Direct Excitation and Sensitizationmentioning

confidence: 99%

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

et al. 2016

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The [2 + 2] photocycloaddition is undisputedly the most important and most frequently used photochemical reaction. In this review, it is attempted to cover all recent aspects of [2 + 2] photocycloaddition chemistry with an emphasis on synthetically relevant, regio-, and stereoselective reactions. The review aims to comprehensively discuss relevant work, which was done in the field in the last 20 years (i.e., from 1995 to 2015). Organization of the data follows a subdivision according to mechanism and substrate classes. Cu(I) and PET (photoinduced electron transfer) catalysis are treated separately in sections 2 and 4, whereas the vast majority of photocycloaddition reactions which occur by direct excitation or sensitization are divided within section 3 into individual subsections according to the photochemically excited olefin.

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Section: Direct Excitation and Sensitizationmentioning

confidence: 99%

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

et al. 2016

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Fenestrane in der Synthese: einzigartige und inspirierende Grundgerüste

et al. 2013

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Das Gerüst von Fenestranen ist einzigartig, da es vier kondensierte Ringe und ein verzerrtes vierfach koordiniertes zentrales Kohlenstoffatom aufweist, dessen Bindungswinkel größer als die regulären 109°28′′ sind. In diesem Kurzaufsatz wird eine detaillierte Übersicht über die Entwicklungen bezüglich dieser Verbindungsklasse, einschließlich ihrer Synthese, für den Zeitraum seit 2006 gegeben. In den vergangenen Jahren wurden Naturstoffe, die als Heterofenestrane klassifiziert werden können, isoliert, und deren Synthesen werden ebenfalls diskutiert.

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Fenestranes in Synthesis: Unique and Highly Inspiring Scaffolds

et al. 2013

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The scaffold of fenestranes is quite unique, as it contains four condensed cycles and a distorted tetracoordinated central carbon atom with bond angles greater than the regular 109°28". In this Minireview, a detailed overview on the developments regarding this compound class, including their synthesis, is given for the time period since 2006. In the past years, natural products that belong to the class of heterofenestranes have been isolated and their syntheses will also be discussed.

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Synthesis and reactions of two stereoisomeric [4.5.5.5]fenestranes with bridgehead substituents

Cited by 8 publications

References 13 publications

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Fenestrane in der Synthese: einzigartige und inspirierende Grundgerüste

Fenestranes in Synthesis: Unique and Highly Inspiring Scaffolds

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Synthesis and reactions of two stereoisomeric [4.5.5.5]fenestranes with bridgehead substituents

Cited by 8 publications

References 13 publications

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Fenestrane in der Synthese: einzigartige und inspirierende Grundgerüste

Fenestranes in Synthesis: Unique and Highly Inspiring Scaffolds

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Product

Resources

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Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions