New Diastereoselective Route to 2‐Substituted cis‐(2S,5S)‐ and trans‐(2S,5R)‐5‐Alkylpyrrolidines as Indolizidine and Pyrrolizidine Scaffolds

Mota, Antonio J.; Chiaroni, A.; Langlois, Nicole

doi:10.1002/ejoc.200300393

Cited by 15 publications

(3 citation statements)

References 62 publications

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“…The alcohol of 5 was protected with a TBDMS group to give silyl ether 6. 12,13 Imidazole was used in the reaction as a catalyst to activate TBDMS-Cl. A small volume of DMF was required to solubilise all the reaction components.…”

Section: Resultsmentioning

confidence: 99%

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Inhibition of prolyl oligopeptidase with a synthetic unnatural dipeptide

Racys¹,

Rea²,

Fülöp³

et al. 2010

Bioorganic & Medicinal Chemistry

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The synthesis of a new inhibitor of prolyl oligopeptidase, containing a piperidine ring, together with an X-ray structure of its complex with the enzyme, is described. This provides evidence that covalent inhibitors of POP do not have to be limited to structures containing 5-membered N-containing heterocyclic rings. inhibitor:Leave this area blank for abstract info. Abstract-A new inhibitor, containing a linked proline-piperidine structure, for the enzyme prolyl oligopeptidase (POP) has been synthesised and demonstrated to bind covalently with the enzyme at the active site. This provides evidence that covalent inhibitors of POP do not have to be limited to structures containing 5-membered N-containing heterocyclic rings.

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Section: Resultsmentioning

confidence: 99%

“…60 Å silica gel (Merck) was used for flash column chromatography. NMR spectra were recorded on a Bruker DPX-400 ( 1 H 400 MHz, 13 C 100 MHz) and Bruker AVII-700 ( 1 H 700 MHz, 13 C 176 MHz) spectrometers unless otherwise specified. Chemical shifts are reported in ppm on the δ scale standardized against TMS, where δ TMS = 0 ppm.…”

Section: Methodsmentioning

confidence: 99%

Inhibition of prolyl oligopeptidase with a synthetic unnatural dipeptide

Racys¹,

Rea²,

Fülöp³

et al. 2010

Bioorganic & Medicinal Chemistry

View full text Add to dashboard Cite

show abstract

“…General Methods. Solvent purification, spectral analyses, and workup procedures were performed as described in the Supporting Information and elsewhere . The chemical shifts in 1 H NMR (300 MHz) and 13 C NMR (75.0 MHz) spectra are given in ppm relative, respectively, to CHCl 3 at 7.27 ppm and to the middle line of CDCl 3 at 77.14 ppm, or as otherwise indicated.…”

Section: Methodsmentioning

confidence: 99%

Diastereoselective Syntheses of Deoxydysibetaine, Dysibetaine, and Its 4-Epimer

Langlois

Nguyen

2004

J. Org. Chem.

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(+/-)-Deoxydysibetaine 2 and 4-epi-dysibetaine 3 were prepared in a few steps from methyl pyroglutamate through a regioselective Mannich reaction at C-2. Natural (2S,4S)-dysibetaine 1, a sponge metabolite isolated from Dysidea herbacea, and (2S)-2 were synthesized from enantiopure (S)-pyroglutaminol with very high stereoselectivity. The key steps were an original formation of stereogenic quaternary center C-2 and the diastereoselective hydroxylation at C-4.

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Desulfonylation Reactions

Alonso

Ájera

2009

Organic Reactions

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The use of sulfones in organic chemistry, acting as an auxiliary group, is still a very important synthetic strategy, especially for the formation of carbon‐carbon single and double bonds. Once the synthetic objective is achieved, the sulfone gruop is usually removed from the molecule. This removal most commonly involves a reductive desulfonylation process with either replacement of the sulfone by hydrogen, or a process that results in the formation of a carbon‐carbon double bond when a β‐hydroxy or β‐alkoxy sulfone is employed. This chapter is devoted to the replacement of the sulfone group by a hydrogen (reductive desulfonylation reactions), and reductive elimination reactions of Julia‐type substrates (Julia‐Lythgoe olefination process). The chapter addresses the full scope, generality, limitations, and synthetic applications of these reactions. The literature through most of 2007 is covered.

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New Diastereoselective Route to 2‐Substituted cis‐(2S,5S)‐ and trans‐(2S,5R)‐5‐Alkylpyrrolidines as Indolizidine and Pyrrolizidine Scaffolds

Cited by 15 publications

References 62 publications

Inhibition of prolyl oligopeptidase with a synthetic unnatural dipeptide

Inhibition of prolyl oligopeptidase with a synthetic unnatural dipeptide

Diastereoselective Syntheses of Deoxydysibetaine, Dysibetaine, and Its 4-Epimer

Desulfonylation Reactions

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