Diels-alder reaction as a synthetic approach to bicyclo[3.3.1]nonane colchicine analogs

Nurieva, E. V.; Semenova, I. S.; Nuriev, V. N.; Shishov, D. V.; Baskin, Igor I.; Zefirova, O. N.; Зефиров, Н. С.

doi:10.1134/s1070428010120213

Cited by 7 publications

(2 citation statements)

References 11 publications

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“…It should be noted that no examples of the formation of tetrahydropyran moiety via domino ring opening of bis(oxiranes) has been found in earlier research. This reaction opens the way to hardly accessible oxabicyclononane derivatives, which, like bicyclononanes [ 31 , 32 ] and azabicyclononanes [ 33 ], represent promising 3D scaffolds for drug design.…”

Section: Resultsmentioning

confidence: 99%

Bis(oxiranes) Containing Cyclooctane Core: Synthesis and Reactivity towards NaN3

et al. 2022

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Reactions of oxirane ring opening provide a powerful tool for regio- and stereoselective synthesis of polyfunctional and heterocyclic compounds, widely used in organic chemistry and drug design. Cyclooctane, alongside other medium-sized rings, is of interest as a novel molecular platform for the construction of target-oriented leads. Additionally, cyclooctane derivatives are well known to be prone to transannular reactions, which makes them a promising object in the search for novel approaches to polycyclic structures. In the present work, a series of cyclooctanediones was studied in Corey-Chaykovsky reactions, and novel spirocyclic bis(oxiranes) containing cyclooctane core, namely, 1,5-dioxadispiro[2.0.2.6]dodecane and 1,8-dioxadispiro[2.3.2.3]dodecane, were synthesized. Ring opening of the obtained bis(oxiranes) upon treatment with sodium azide was investigated, and it was found that the reaction path is determined by the reciprocal orientation of oxygen atoms in the oxirane moieties. Diastereomers of the bis(oxiranes) with cis-orientation underwent independent ring opening, supplying corresponding diazidodiols, while in the case of stereoisomers with trans-orientation, domino-like reactions occurred, including intramolecular nucleophilic attack and the formation of a novel three- or six-membered O-containing ring. Summarily, a straightforward approach to polyfunctional compounds containing cyclooctane or oxabicyclo[3.3.1]nonane cores, employing bis(oxiranes), was elaborated.

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Section: Resultsmentioning

confidence: 99%

Bis(oxiranes) Containing Cyclooctane Core: Synthesis and Reactivity towards NaN3

et al. 2022

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“…The base-catalyzed hydrolysis of this lactone then yielded an endo-hydroxy carboxylic acid 452 (Scheme 103). 200 The fragmentation of 1,3-adamantanediol (453) is also another useful procedure to achieve functionalized bicyclo[3. condition, they differ in their area of application. Honda and coworkers in their two successive articles exemplied this fact in detail.…”

Section: O-cyclizationmentioning

confidence: 99%

Different routes for the construction of biologically active diversely functionalized bicyclo[3.3.1]nonanes: an exploration of new perspectives for anticancer chemotherapeutics

et al. 2023

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Formation of Alkenes by Diels–Alder Reactions

Larock

2018

Comprehensive Organic Transformations

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General Reviews Regioselectivity Exo / Endo Selectivity Asymmetric Diels–Alder Reaction Mechanism Use of High Pressure Microwave Irradiation Infrared Irradiation Mechanical Ball Milling Ultracentrifugation Use of Ultrasound Catalysis Solvent Effects Cavity Effects Retro‐Diels–Alder Reaction Intramolecular Diels–Alder Reaction Inverse Electron‐Demand Diels–Alder Reaction Radical Cation Diels–Alder Reaction Ionic Diels–Alder Reaction Use of Heterodienophiles Use of Heteroatom‐Containing “Dienes” Use of Substituted 1,3‐Dienes o ‐Quinodimethanes and Heterocyclic Analogues Arynes and Hetarynes Some Other Dienophiles Dienophile Equivalents Transition Metal Carbenes as Dienophiles

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Diels-alder reaction as a synthetic approach to bicyclo[3.3.1]nonane colchicine analogs

Cited by 7 publications

References 11 publications

Bis(oxiranes) Containing Cyclooctane Core: Synthesis and Reactivity towards NaN3

Bis(oxiranes) Containing Cyclooctane Core: Synthesis and Reactivity towards NaN3

Different routes for the construction of biologically active diversely functionalized bicyclo[3.3.1]nonanes: an exploration of new perspectives for anticancer chemotherapeutics

Formation of Alkenes by Diels–Alder Reactions

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