Five‐Membered Carbocycles

Nair, Vijay; Paul, Rony Rajan; Rodríguez, Jean; Bonne, Damien

doi:10.1002/9781119006220.ch6

Cited by 5 publications

(1 citation statement)

References 61 publications

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“…Capnellene 29 and its hydroxy derivatives, which belong to the linearly fused triquinane sesquiterpene family, have drawn the interest of synthetic chemists for decades. − They possess a geminal methyl unit at Cl and an angular methyl group at C4 (Scheme ).…”

Section: Synthesismentioning

confidence: 99%

Tricyclic Sesquiterpenes from Marine Origin

et al. 2017

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The structure elucidation, biosynthesis, and biological activity of marine carbotricyclic sesquiterpene compounds are reviewed from the pioneering results to the end of 2015. Their total syntheses with a particular emphasis on the first syntheses, enantiomeric versions, and syntheses that led to the revision of structures or stereochemistries are summarized. Overall, 284 tricyclic compounds are classified into fused, bridged, and miscellaneous structures based on 54 different skeletal types. Tricyclic sesquiterpenes constitute an important group of natural products. Their structural diversity and biological activities have generated further interest in the field of drug discovery research, although the exact mechanisms of action of these species are not well known. Furthermore, these tricyclic structures, according to their chemical complexity, are a source of inspiration for chemists in the field of total synthesis for the development of innovative methodologies.

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Section: Synthesismentioning

confidence: 99%

Tricyclic Sesquiterpenes from Marine Origin

et al. 2017

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Tandemreaktionen aus anionischer Oxy‐Cope‐Umlagerung und Oxygenierung als vielseitiger Zugang zu verschiedenartigen Gerüsten

et al. 2020

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Tandemreaktionen aus anionischer Oxy‐Cope‐Umlagerung und Radikaloxygenierung ergeben δ,ϵ‐ungesättigte α‐(Aminoxy)carbonylverbindungen, die sich als vielseitige Vorläufer für verschiedenartige Verbindungsklassen eignen. Funktionalisierte Carbocyclen werden durch sehr seltene 5‐endo‐trig, aber auch gebräuchlichere 5‐exo‐trig Radikalcyclisierungen durch Nutzung des persistenten Radikaleffekts erhalten. Die Tandemreaktionen können durch hochdiastereoselektive Allylierungs‐ oder Reduktionsschritte erweitert werden, die zu komplexen Gerüsten führen.

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Synthesis of Cyclopentene Derivatives via Electrochemically Induced Intermolecular Selective (3+2) Annulation

Guan

Zhu

et al. 2022

Angewandte Chemie

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Cyclopentenes are common cores in many natural products, and in bioactive and functional molecules. However, their synthesis remains challenging in terms of harsh conditions, poor selectivity, prefunctionalization of the substrates, over-reliance on volatile activating reagents and the use of noble metals. Herein, we develop an electrochemical mediator-induced intermolecular selective (3+2) annulation of readily available alkenes and alkynes/alkenes, which provides a simple and efficient method for the synthesis of a library of decorated cyclopentenes and cyclopentanes. This protocol features high efficiency, mild reaction conditions, broad substrate scope, good functional group tolerance, and high regioselectivity. Potential applications are demonstrated by gram-scale synthesis as well as the construction of structural diversity and complexity. A preliminary mechanistic investigation was performed, which indicated that an iodine radical and carbon radicals are involved in this transformation.

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Five‐Membered Carbocycles

Cited by 5 publications

References 61 publications

Tricyclic Sesquiterpenes from Marine Origin

Tricyclic Sesquiterpenes from Marine Origin

Tandemreaktionen aus anionischer Oxy‐Cope‐Umlagerung und Oxygenierung als vielseitiger Zugang zu verschiedenartigen Gerüsten

Synthesis of Cyclopentene Derivatives via Electrochemically Induced Intermolecular Selective (3+2) Annulation

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