Cascading pericyclic reactions: building complex carbon frameworks for natural product synthesis

Arns, Steve; Barriault, Louis

doi:10.1039/b700054p

Cited by 64 publications

(13 citation statements)

References 69 publications

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“…[22] Although a deprotonation would fit within the concept of catalysis, even if the base were used stoichiometrically, we have excluded clearly irreversible examples that utilize bases (e.g. NaH, n BuLi), unless such bases are used substoichiometrically.…”

Section: [33]-sigmatropic Rearrangementsmentioning

confidence: 99%

“…[21c] Under thermal conditions, tandem pericyclic processes were combined with oxy-Cope rearrangements in complex cascade sequences to great success. [22] Although a deprotonation would fit within the concept of catalysis, even if the base were used stoichiometrically, we have excluded clearly irreversible examples that utilize bases (e.g. NaH, nBuLi), unless such bases are used substoichiometrically.…”

Section: Oxy-cope Rearrangementsmentioning

confidence: 99%

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Toward a Symphony of Reactivity: Cascades Involving Catalysis and Sigmatropic Rearrangements

et al. 2014

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Catalysis and synthesis are intimately linked in modern organic chemistry. The synthesis of complex molecules is an ever evolving area of science. In many regards, the inherent beauty associated with a synthetic sequence can be linked to a certain combination of the creativity with which a sequence is designed and the overall efficiency with which the ultimate process is performed. In synthesis, as in other endeavors, beauty is very much in the eyes of the beholder.[**] It is with this in mind that we will attempt to review an area of synthesis that has fascinated us and that we find extraordinarily beautiful, namely the combination of catalysis and sigmatropic rearrangements in consecutive and cascade sequences.

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Section: [33]-sigmatropic Rearrangementsmentioning

confidence: 99%

Section: Oxy-cope Rearrangementsmentioning

confidence: 99%

Toward a Symphony of Reactivity: Cascades Involving Catalysis and Sigmatropic Rearrangements

et al. 2014

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“…Außerdem fand Evans heraus, dass anionische Alkoxide die Reaktionsgeschwindigkeit noch stärker erhöhen 21c. Unter thermischen Bedingungen wurden pericyclische Tandemprozesse mit großem Erfolg in komplexen Kaskadensequenzen mit Oxy‐Cope‐Umlagerungen kombiniert 22. Obwohl eine Deprotonierung sogar unter Verwendung stöchiometrischer Mengen an Base in das Katalysekonzept passen würde, lassen wir Beispiele unberücksichtigt, in denen Basen verwendet werden (z.…”

Section: [33]‐sigmatrope Umlagerungenunclassified

Bis hin zu einer Symphonie der Reaktivität: Kaskaden mit Katalysen und sigmatropen Umlagerungen

et al. 2014

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Die Katalyse und die Synthese sind in der modernen organischen Chemie eng miteinander verbunden. Die Synthese komplexer Moleküle ist ein sich ständig weiterentwickelndes Gebiet. In vielerlei Hinsicht kann die inhärente Schönheit einer Synthesesequenz mit einer bestimmten Kombination aus Kreativität, mit der eine Sequenz entworfen wurde, und der Gesamteffizienz, mit der das endgültige Verfahren durchgeführt wird, in Zusammenhang gebracht werden. Ebenso wie bei anderen Unterfangen liegt bei chemischen Synthesen die Schönheit im Auge des Betrachters. In diesem Sinne werden wir versuchen, ein Gebiet der Synthese zu erörtern, das uns fasziniert, und das wir außergewöhnlich schön finden, nämlich die Kombination aus Katalyse und sigmatropen Umlagerungen in konsekutiven Sequenzen und Kaskadenreaktionen.

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“…During their studies towards the synthesis of highly functionalized bicyclo[m.n.1] alkanones, Arns and Barriault ingeniously devised and successfully implemented a Lewis acid mediated triple domino reaction that involved a Diels-Alder/Prins/pinacol cascade. [71] This process enabled the preparation of a variety of bridged polycyclic structures closely resembling the core structures of a number of natural products (Scheme 23). [72] In particular, treatment of the 5,6-bicyclic alkenylketal 219 with SnCl 4 smoothly delivered bridged tricyclic ketone 222 in 53 % yield.…”

Section: Barriault's Cationic Cyclization Cascadementioning

confidence: 99%

The Chemistry of the Polycyclic Polyprenylated Acylphloroglucinols

2012

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With their fascinating biological profiles and stunningly complex molecular architectures, the polycyclic polyprenylated acylphloroglucinols (PPAPs) have long provided a fertile playing field for synthetic organic chemists. In particular, the recent advent of innovative synthetic methods and strategies together with C-C bond-forming reactions and asymmetric catalysis have revitalized this field tremendously. Consequently, PPAP targets which once seemed beyond reach have now been synthesized. This Review aims to highlight the recent achievements in the total synthesis of PPAPs, as well as notable methods developed for the construction of the bicyclo[3.3.1] core of these chemically and biologically intriguing molecules.

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Cascading pericyclic reactions: building complex carbon frameworks for natural product synthesis

Cited by 64 publications

References 69 publications

Toward a Symphony of Reactivity: Cascades Involving Catalysis and Sigmatropic Rearrangements

Toward a Symphony of Reactivity: Cascades Involving Catalysis and Sigmatropic Rearrangements

Bis hin zu einer Symphonie der Reaktivität: Kaskaden mit Katalysen und sigmatropen Umlagerungen

The Chemistry of the Polycyclic Polyprenylated Acylphloroglucinols

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