3-Alkyl-1,2-cyclopentanediones by Negishi cross-coupling of a 3-bromo-1,2-cyclopentanedione silyl enol ether with alkylzinc reagents: an approach to 2-substituted carboxylic acid γ-lactones, homocitric and lycoperdic acids

Paju, Anne; Kostomarova, Diana; Matkevits, Katharina; Laos, Marit; Pehk, Tõnis; Kanger, Tõnis; Lopp, Margus

doi:10.1016/j.tet.2015.10.014

Cited by 14 publications

(6 citation statements)

References 63 publications

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“…To determine the best catalyst system for formation of 8 , we compared 1 H NMR spectra of crude Negishi product mixtures after aqueous workup for various catalyst combinations using bromobenzene as a model coupling partner. On the basis of results by Paju, 85 we tested Pd 2 (dba) 3 /QPhos alongside other commonly used catalyst combinations, including PdCl 2 (dppf) and Pd(Ph 3 P) 4 . We found that the latter two were vastly inferior, giving negligible amounts of desired 8.…”

Section: Resultsmentioning

confidence: 99%

Reevaluating the Substrate Specificity of the L-Type Amino Acid Transporter (LAT1)

et al. 2018

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The L-type amino acid transporter 1 (LAT1, SLC7A5) transports essential amino acids across the blood-brain barrier (BBB) and into cancer cells. To utilize LAT1 for drug delivery, potent amino acid promoieties are desired, as prodrugs must compete with millimolar concentrations of endogenous amino acids. To better understand ligand-transporter interactions that could improve potency, we developed structural LAT1 models to guide the design of substituted analogues of phenylalanine and histidine. Furthermore, we evaluated the structure-activity relationship (SAR) for both enantiomers of naturally occurring LAT1 substrates. Analogues were tested in cis-inhibition and trans-stimulation cell assays to determine potency and uptake rate. Surprisingly, LAT1 can transport amino acid-like substrates with wide-ranging polarities including those containing ionizable substituents. Additionally, the rate of LAT1 transport was generally nonstereoselective even though enantiomers likely exhibit different binding modes. Our findings have broad implications to the development of new treatments for brain disorders and cancer.

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Section: Resultsmentioning

confidence: 99%

Reevaluating the Substrate Specificity of the L-Type Amino Acid Transporter (LAT1)

et al. 2018

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“…4 We have used these molecules as starting materials/platform molecules for making new high value-added fine chemicals, such as nucleoside analogues 5 and several bioactive natural compounds 6 and their analogues. 7 On the other hand, aminocatalysis has been an important research topic for 10 years, providing the most widely used organocatalysts in the field. 8 We have previously shown that a Mukaiyama-Michael addition reaction of cyclopentane-1,2-dione dienol silyl ethers proceeds in an organocatalytic way with α,β-unsaturated aldehydes.…”

Section: Ohmentioning

confidence: 99%

“…Following GPB from 2i (trans/cis 7:1) gave 5i after purification as a white amorphous solid; yield: 18 mg (55%); ratio trans/cis 7:1; transisomer 46% ee; cis-isomer 73% ee [HPLC (Phenomenex Lux® 3μm amylose-2, hexane/EtOH 8:2, 1 mL/min, 254 nm): t R = 7.8 (major trans), 20.0 (minor trans), 7…”

Section: Paper Syn Thesismentioning

confidence: 99%

Asymmetric Organocatalytic Michael Addition–Cyclization Cascade of Cyclopentane-1,2-dione with Substituted α,β-Unsaturated Aldehydes

et al. 2017

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An asymmetric organocatalytic Michael addition–cyclization cascade reaction has been developed using cyclopentane-1,2-dione as a Michael donor and α,β-unsaturated aldehydes as Michael acceptors. Bicyclic hemiacetals were obtained in excellent yields and enantioselectivities. On the basis of the results, a one-pot reaction has been developed to obtain chiral 3-substituted cyclopentane-1,2-diones and substituted dihydropyrans in good yields and excellent enantioselectivity.

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“…In 2004, the first instance of using CPD as a precursor for high value-added fine chemicals such as a homocitric acid lactone was published by our group [19]. Since then we have developed synthetic pathways for lycoperdic acid [20] and nucleoside analogues [21] starting from CPD. The organocatalytic methods for the synthe- sis of substituted cyclopentane diones were uninvestigated until 2014 when we showed that CPD undergoes a Michael addition with nitrostyrenes [22].…”

Section: Introductionmentioning

confidence: 99%

Asymmetric organocatalytic Michael addition of cyclopentane-1,2-dione to alkylidene oxindole

Silm¹,

Järving²,

Kanger³

2022

Beilstein J. Org. Chem.

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3-Alkyl-1,2-cyclopentanediones by Negishi cross-coupling of a 3-bromo-1,2-cyclopentanedione silyl enol ether with alkylzinc reagents: an approach to 2-substituted carboxylic acid γ-lactones, homocitric and lycoperdic acids

Cited by 14 publications

References 63 publications

Reevaluating the Substrate Specificity of the L-Type Amino Acid Transporter (LAT1)

Reevaluating the Substrate Specificity of the L-Type Amino Acid Transporter (LAT1)

Asymmetric Organocatalytic Michael Addition–Cyclization Cascade of Cyclopentane-1,2-dione with Substituted α,β-Unsaturated Aldehydes

Asymmetric organocatalytic Michael addition of cyclopentane-1,2-dione to alkylidene oxindole

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