146864-12-2Relevant articles and documents
A selective synthesis of fluorinated cispentacin derivatives
Kiss, Lorand,Nonn, Melinda,Forro, Eniko,Sillanpaeae, Reijo,Fustero, Santos,Fueloep, Ferenc
, p. 4070 - 4076 (2014/07/08)
A facile selective method has been developed for the synthesis of new fluorine-containing cispentacin stereoisomers. Mono- and difluorinated cispentacin derivatives were synthetized from a bicyclic β-lactam in five or six steps involving a regio- and stereoselective hydroxylation through iodooxazoline formation, followed by deoxygenation by fluorination. Starting from an enantiomerically pure bicyclic β-lactam obtained by enzymatic resolution of the racemic compound, an enantiodivergent procedure allowed the preparation of both dextro- and levorotatory difluorinated cispentacins. Mono- and difluorinated cispentacin derivatives were synthetized from a bicyclic β-lactam in five or six steps. An enantiodivergent procedure allowed the preparation of both dextro- and levorotatory difluorinated cispentacins. Copyright
A de Novo stereocontrolled approach to syn- and anti-disubstituted acyclic β2,3-amino acid enantiomers
Cherepanova, Maria,Kiss, Loránd,Forr?, Eniko,Fül?p, Ferenc
, p. 403 - 409 (2014/01/23)
The stereocontrolled syntheses of functionalized acyclic β2,3-amino acid derivatives in enantiomerically pure form were performed by starting from enantiopure cis- and trans-2-aminocyclopent-3- enecarboxylates, which were derived from a racemic bicyclic β-lactam. The synthetic strategy involves the stereoselective dihydroxylaton of the C-C double bond of the cyclopentene β-amino esters. The subsequent NaIO 4-mediated ring cleavage affords dialdehyde intermediates that undergo functionalization by a Wittig reaction. The stereocontrolled syntheses of functionalized acyclic β2,3-amino acid derivatives in enantiomerically pure form have been performed in five steps by starting from enantiopure cis- and trans-2-aminocyclopent-3-enecarboxylates, which were derived from a racemic bicyclic β-lactam. Copyright
A de Novo Stereocontrolled Approach to syn- and anti-Disubstituted Acyclic β2,3-Amino Acid Enantiomers
Cherepanova, Maria,Kiss, Lornd,Forr, Eniko,Fül?p, Ferenc
, p. 403 - 409 (2015/10/05)
The stereocontrolled syntheses of functionalized acyclic β2,3-amino acid derivatives in enantiomerically pure form were performed by starting from enantiopure cis- and trans-2-aminocyclopent-3-enecarboxylates, which were derived from a racemic bicyclic β-lactam. The synthetic strategy involves the stereoselective dihydroxylaton of the C-C double bond of the cyclopentene β-amino esters. The subsequent NaIO4-mediated ring cleavage affords dialdehyde intermediates that undergo functionalization by a Wittig reaction.
Synthesis of novel isoxazoline-fused cyclic β-amino esters by regio- and stereo-selective 1,3-dipolar cycloaddition
Nonn, Melinda,Kiss, Loránd,Forró, Enik?,Mucsi, Zoltán,Fül?p, Ferenc
scheme or table, p. 4079 - 4085 (2011/06/24)
Isoxazoline-fused 2-aminocyclopentanecarboxylate derivatives were regio- and stereo-selectively synthesized by nitrile oxide 1,3-dipolar cycloaddition to cis- or trans-ethyl-2-aminocyclopent-3-enecarboxylates. The compounds were prepared in enantiomerical
Novel functionalized cispentacin derivatives. Synthesis of 1,2,3-triazole-substituted 2-aminocyclopentanecarboxylate stereoisomers
Kiss, Lorand,Forro, Eniko,Sillanpaeae, Reijo,Fueloep, Ferenc
experimental part, p. 2856 - 2860 (2009/07/04)
Four 1,2,3-triazole-substituted ethyl 2-amino-3-hydroxycyclopentanecarboxylate diastereomers (3,4-disubstituted cispentacins) with a cyclopentane skeleton were prepared in enantiomerically pure form from racemic β-lactam 7 via enzymatic ring opening, epoxidation and selective ring opening of the oxirane ring with sodium azide. The formation of the 1,2,3-triazole ring system involved click chemistry: 1,3-dipolar cycloaddition of the corresponding 4-substituted azidocarboxylates with diethyl acetylenedicarboxylate.
Vapour-assisted enzymatic hydrolysis of β-lactams in a solvent-free system
Forro, Eniko,Fueloep, Ferenc
, p. 1005 - 1009 (2008/09/21)
A new, solvent-free, vapour-assisted method, developed for the synthesis of carbocyclic cis β-amino acid enantiomers through the Candida antarctica lipase B-catalysed enantioselective (E >200) hydrolysis of β-lactams with 0.5 equiv of H2O at 70 °C, has been demonstrated to be applicable on a preparative scale to produce (±)-2 (the starting racemate for cispentacin), (±)-3 (the starting racemate for 4-tert-butylcispentacin, a new cispentacin analogue) and (±)-7 (the starting racemate for 1,4-ethylene-bridged cispentacin).
Diastereo- and enantioselective synthesis of orthogonally protected 2,4-diaminocyclopentanecarboxylates: A flip from β-amino- to β,γ-diaminocarboxylates
Kiss, Lorand,Forro, Eniko,Sillanpaeae, Reijo,Fueloep, Ferenc
, p. 8786 - 8790 (2008/03/13)
(Chemical Equation Presented) Conformationally restricted, orthogonally protected 2,4-diaminocarboxylates with a cyclopentane skeleton were efficiently synthesized from β-lactam 6, the syntheses involving strategies of diastereoselective epoxidation of th
Advanced procedure for the enzymatic ring opening of unsaturated alicyclic β-lactams
Forro, Eniko,Fueloep, Ferenc
, p. 2875 - 2880 (2007/10/03)
Enantiopure β-amino acids 1a-4a and β-lactams 1b-4b were prepared simultaneously through the lipolase-catalysed enantioselective ring opening of unsaturated racemic β-lactams (±)-1-(±)-4. High enantioselectivities (E>200) were observed when the reactions
Novel 1,2-disubstituted carbocyclic nucleoside analogues of purine with a cyclopentene ring
Besada,Gonzalez-Moa,Teran,Santana,Uriarte
, p. 2445 - 2449 (2007/10/03)
A total and versatile synthesis of a new series of carbocyclic nucleoside analogues which are derivatives of purine with a 1,2-disubstituted cyclopentene ring (I) is described. The 6-chloropurine derivatives 3 and 9 were prepared by construction of the heterocyclic base about the primary amino group of the (±)-cis-2-amino-3-cyclopentenylmethanol (1), which was synthesized in good yield from cyclopentadiene in four steps. The substitution of a chlorine atom in the compounds 3 and 9 by an amino group (compounds 4 and 10) and by a hydroxyl group (compounds 5 and 11) was carried out with NH4OH or with NaOH, respectively.
