Reversible Cyclopropane Ring‐Cleavage Reactions within Etheno‐Bridged [4.3.1]Propelladiene Frameworks Leading to Aza‐ and Oxa‐[5.6.5.6]fenestratetraenes

Heinrich, Nora; Willis, Anthony C.; Cade, Ian A.; Ho, Junming; Coote, Michelle L.; Banwell, Martin G.

doi:10.1002/chem.201202903

Cited by 7 publications

(3 citation statements)

References 11 publications

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“…3 ),5 and asperaculin A 4 6 have made fenestranes appealing synthetic targets. Thus, several noteworthy methods have been developed for the synthesis of fenestranes with a full‐carbon scaffold7 and fenestranes containing heteroatoms (oxafenestranes8 and azafenestranes) 8c,d. 9 However, the synthesis of chiral nonracemic fenestranes remains challenging, and only a few oxafenestranes have been synthesized as single enantiomers8a,b,e and no enantioselective methods for the synthesis of full‐carbon fenestranes have been reported 3a…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Bridged Oxafenestranes from Pleuromutilin

2014

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Fenestranes are an intriguing class of highly strained molecules possessing a quaternary carbon with bonds that deviate from the canonical tetrahedral geometry. Herein we report the discovery that the natural product pleuromutilin can be used as a structurally complex starting material for the synthesis of a series of bridged cis,cis,cis,cis-[4.5.5.5]- and cis,cis,cis,cis-[4.5.7.5]oxafenestranes through a carbocation rearrangement cascade. X-ray crystallographic analysis of several cis,cis,cis,cis-[4.5.5.5]oxafenestranes shows a significant planarization of the central tetracoordinate carbon atom and demonstrates the influence of bridgehead substituents and bridging rings on planarity.

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Section: Methodsmentioning

confidence: 99%

Synthesis of Bridged Oxafenestranes from Pleuromutilin

2014

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“…Während der Synthese des biologisch aktiven Neoclerodans Salvileucalin B ( 74 ), das ein [5.3.1]Propellan enthält, fanden Banwell und Mitarbeiter einen Zugang zu Aza‐ und Oxa‐[5.6.5.6]Fenestratetraenen 80 – 83 durch sigmatrope Umlagerungen (Schema ) 67…”

Section: Neue Beispiele Synthetischer Fenestraneunclassified

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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“…Working on the synthesis of the [5.3.1]propellane-containing and biologically active neoclerodane salvileucalin B (74), Banwell and co-workers found an access to aza-and oxa-[5.6.5.6]fenestratetraenes 80-83 through sigmatropic rearrangements (Scheme 12). [67] The attempted conversion of 75 to 73 by treatment with DIBAl-H did not give the desired product, but both [5.6.5.6]fenestratetraenes 81 and 82 instead. Mechanistic considerations lead to a pathway that involves sigmatropic and allylic rearrangements as well as cleavage of the cyclopropane ring.…”

Section: Methodsmentioning

confidence: 99%

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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Reversible Cyclopropane Ring‐Cleavage Reactions within Etheno‐Bridged [4.3.1]Propelladiene Frameworks Leading to Aza‐ and Oxa‐[5.6.5.6]fenestratetraenes

Cited by 7 publications

References 11 publications

Synthesis of Bridged Oxafenestranes from Pleuromutilin

Synthesis of Bridged Oxafenestranes from Pleuromutilin

Fenestrane in der Synthese: einzigartige und inspirierende Grundgerüste

Fenestranes in Synthesis: Unique and Highly Inspiring Scaffolds

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