New approach to asymmetrically substituted methoxypyrazines, derivatives of wine flavors

Candelon, Nicolas; Shinkaruk, Svitlana; Bennetau, Bernard; Bennetau-Pelissero, Catherine; Dumartin, Marie-Laurence; Degueil, Marie; Babin, Pierre

doi:10.1016/j.tet.2010.01.088

Cited by 9 publications

(5 citation statements)

References 31 publications

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“…The reason for it was that peptidoaldehydes reacted in two ways: as components for the PS cyclization, but also as substrates for side intramolecular cyclization. Peptidoaldehydes are very sensitive to the presence of acid (Scheme ) and undergo intramolecular cyclization and elimination . The side products were isolated (~20%) and determined as enamides 13 .…”

Section: Resultsmentioning

confidence: 99%

Peptides and peptidoaldehydes as substrates for the Pictet–Spengler reaction

Pulka

Slupska

Puszko

et al. 2013

Journal of Peptide Science

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The Pictet-Spengler (PS) reaction was performed with various types of substrates: H-Trp-OMe and dipeptides with N-terminal Trp as arylethylamine components and Z-protected amino aldehydes and peptidoaldehydes as carbonyl components. We found that the C-terminal part of Trp derivatives did not have any influence on the stereoselectivity of the reaction and the results are the same for simple esters of Trp and dipeptides. On the contrary, the selectivity of the PS reaction with peptidoaldehydes with L configuration of the C-terminus residue is totally different from that obtained with simple L-amino aldehydes. It allows us to obtain cis stereoisomers, which cannot be isolated from the reaction with amino aldehydes. But the utility of the peptidoaldehydes as substrates for the PS reaction is reduced by the side formation of enamides which decrease the yield of cyclization.

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Section: Resultsmentioning

confidence: 99%

Peptides and peptidoaldehydes as substrates for the Pictet–Spengler reaction

Pulka

Slupska

Puszko

et al. 2013

Journal of Peptide Science

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“…Several syntheses of methoxypyrazines using as starting materials DKPs or related compounds have been described in the literature. 17 In the same line, an elegant synthesis-guided structure revision of the sarcodonin natural product family has been reported, involving the construction of a hydroxypyrazine from a DKP. 18…”

Section: Synthetic Sequences Initiated By the Formation Of Dkp Lactim...mentioning

confidence: 99%

Privileged scaffolds in synthesis: 2,5-piperazinediones as templates for the preparation of structurally diverse heterocycles

et al. 2012

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“…Also, the availability of stereochemically pure aroma compounds and/or epitopes thereof permits a proper stereochemical characterization of food flavors and fragrances that is important to establish the genuineness, geographic origin, biogenesis, and quality of products [6][7][8]. Therefore, novel synthetic routes towards optically pure food ingredients are continuously being developed by industry and academia [9][10][11][12]; significantly, biocatalysis plays a major role in this field of research [13,14]. Indeed, aroma compounds such as linalool and ␣-terpineol displaying a chiral tertiary alcohol functionality, that is a structural motif widespread among many natural products including flavor compounds, are typically prepared using hydrolases for the kinetic resolution of racemates [15][16][17][18][19].…”

Section: Introductionmentioning

confidence: 99%