Solid-Phase Olefin Cross-Metathesis Promoted by a Linker

Garner, Amanda L.; Koide, Kazunori

doi:10.1021/ol702415x

Cited by 23 publications

(11 citation statements)

References 34 publications

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“…[34] Whereas attachment of an olefin through a long carbon chain could, in principle, facilitate intrabead homodimerization, use of a short carbon chain could also impact metathesis efficiency because of steric hindrance. [34] Whereas attachment of an olefin through a long carbon chain could, in principle, facilitate intrabead homodimerization, use of a short carbon chain could also impact metathesis efficiency because of steric hindrance.…”

Section: Solid-phase Cross-metathesis Reactionsmentioning

confidence: 99%

“…In particular, the effect of the distance between the polymer matrix and the alkene moiety of a supported olefin on CM reactions was studied by Koide and Garner. [34] Whereas attachment of an olefin through a long carbon chain could, in principle, facilitate intrabead homodimerization, use of a short carbon chain could also impact metathesis efficiency because of steric hindrance. To study this proximity effect they evaluated CM between alkenes 63a, bound to a trityl chloride resin (0.94-0.98 mmol g -1 ), and non-terminal olefin 64 (Scheme 16).…”

Section: Solid-phase Cross-metathesis Reactionsmentioning

confidence: 99%

See 1 more Smart Citation

Cross‐Metathesis on Immobilized Substrates – Application to the Generation of Synthetically and Biologically Relevant Structures

Riveira

Mata

2017

Eur J Org Chem

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Olefin metathesis constitutes a seemingly endless area of research that has had an enormous impact on several branches of chemistry, both in industry and in academia. Once the potential of this reaction as a carbon–carbon bond‐forming tool was widely recognized, its adaptation to solid‐phase chemistry naturally followed. This review documents the applications and possibilities that polymer‐bound alkenes have provided in the challenging cross‐version of olefin metathesis, through efforts that are far from exhausted.

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Section: Solid-phase Cross-metathesis Reactionsmentioning

confidence: 99%

Section: Solid-phase Cross-metathesis Reactionsmentioning

confidence: 99%

Cross‐Metathesis on Immobilized Substrates – Application to the Generation of Synthetically and Biologically Relevant Structures

Riveira

Mata

2017

Eur J Org Chem

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“…5). Chang et al [46] utilized CM for the synthesis of hydroxyl (E)-stilbenoids, Garner and Koide [47] in the synthesis of quinines, and Mendez and Mata [48] for the generation of biologically relevant chalcones. Brown et al [49] applied a RCMcleavage strategy for the synthesis of cyclic sulfonamides.…”

Section: Introductionmentioning

confidence: 99%

Metathesis Reactions on Solid-Phase: Towards New Synthesis Challenges

Franzén

2016

Top Catal

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Today there are many types of transition-metalcatalyzed carbon-carbon bond-forming reactions. Of these, the olefin metathesis has made possible a wide range of transformations with commercially available and easily handled catalysts. Olefin metathesis is widely considered as one of the most powerful synthetic tool in organic chemistry. During the last 20 years many new catalysts with excellent selectivity and efficiency have been developed, also to be used in solid phase organic chemistry protocols. The understanding of the mechanisms and interactions between the catalyst and substrate has resulted that an increasing number of research groups have employed these reactions in multistep procedures and in the synthesis of active pharmaceutical ingredients and natural products. Although the olefin metathesis reaction still proceeds better in homogeneous phase, some structural modifications of the catalyst and new approaches for immobilization have provided interesting possibilities towards more efficient use also in heterogeneous phase. To celebrate 10 years since the Nobel Prize in Chemistry given to Yves Chauvin, Richard Schrock and Robert Grubbs for the ''development of the metathesis method in organic synthesis'' and to summarize recent results obtained in the field of solid phase metathesis chemistry this short review was written.Keywords Olefin metathesis Á Heterogeneous catalysis Á Solid supported catalyst Á Carbon-carbon bonds BackgroundSolid phase ring-closing metathesis (RCM) was first time applied for the synthesis of seven membered cycloolefins in 1996 by van Maarseveen et al. [1]. This cyclization/cleavage approach proceeded in a moderate 54 % yield, due to intermolecular ''metathetical dimerizations'' at the resin according to the authors. As the catalyst, the well-known and utilized ruthenium carbene complex described by Grubbs and co-authors [2-4] was used. A few years later, this strategy was further utilized for the preparation of unsaturated a-estersubstituted N-heterocycles from solid phase-bound olefinic amino acid derivatives.[5] and for the preparation of b-turn mimetics [6] (Fig. 1). The methodology has more recently been used for the macrocyclization strategies to obtain peptide-peptoid hydrid-molecules [7] On the other hand, the ringopening cross metathesis (ROM) of bicyclic alkenes with terminal aryl alkenes on solid support described in 1997 by Cuny et al. [8] is a excellent example of a highly regioselective reaction, marking the start for the utilization of metathesis reactions on solid phase of this reaction-type. Robert Grubbs and co-authors [9-11] described the same year, that norbornyl monomers polymerize readily at ROM conditions. This gave the starting point also for ring-opening metathesis polymerization (ROMP) that found applications for example in the preparation of terpyridine-based silica supports [12], and norbornene-based resins for applications in organic synthesis and other different immobilized polymers [13,14] (Fig. 2). Towards More Complicated StructuresSeeberger and c...

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“…13,14,15,16 Attempts to tailor biological activity by alkene derivatization are less common. 17,18 Bhattacharjee and coworkers have put forth a CATALYST-generated binding model that indicates the alkene portion may be important for QN’s activity, despite being spatially distant from the remaining functional groups. 19 However, Alumasa et al 9 recently showed the alkene functionality to be nonessential for binding to free heme, the putative drug target of QN and other quinoline antimalarials.…”

Section: Introductionmentioning

confidence: 99%

Investigating the activity of quinine analogues versus chloroquine resistant Plasmodium falciparum

Dinio

Gorka

McGinniss

et al. 2012

Bioorganic & Medicinal Chemistry

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Plasmodium falciparum, the deadliest malarial parasite species, has developed resistance against nearly all man-made antimalarial drugs within the past century. However, quinine (QN), the first antimalarial drug, remains efficacious worldwide. Some chloroquine resistant (CQR) P. falciparum strains or isolates show mild cross resistance to QN, but many do not. Further optimization of QN may provide well-tolerated therapy with improved activity vs. CQR malaria. Thus, using the Heck reaction, we have pursued a structure-activity relationship study, including vinyl group modifications of QN. Certain derivatives show good antiplasmodial activity in QN-resistant and QN-sensitive strains, with lower IC50 values relative to QN.

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Solid-Phase Olefin Cross-Metathesis Promoted by a Linker

Cited by 23 publications

References 34 publications

Cross‐Metathesis on Immobilized Substrates – Application to the Generation of Synthetically and Biologically Relevant Structures

Cross‐Metathesis on Immobilized Substrates – Application to the Generation of Synthetically and Biologically Relevant Structures

Metathesis Reactions on Solid-Phase: Towards New Synthesis Challenges

Investigating the activity of quinine analogues versus chloroquine resistant Plasmodium falciparum

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