350015-75-7Relevant academic research and scientific papers
Preparation of (1R,8S)- and (1S,8R)-9-azabicyclo[6.2.0]dec-4-en-10-one: Potential starting compounds for the synthesis of anatoxin-a
Forro, Eniko,Arva, Judit,Fueloep, Ferenc
, p. 643 - 649 (2001)
9-Azabicyclo[6.2.0]-dec-4-en-10-one (±)-2, obtained from cyclooctadiene by addition of chlorosulfonyl isocyanate, was N-hydroxymethylated to (±)-3 and then resolved by lipase-catalysed asymmetric acylation of the primary OH group at the (S)-stereogenic centre. High enantioselectivity (E = 94) was observed when lipase PS and vinyl butyrate were used in di-iso-propyl ether at -15°C, resulting in the enantiomerically enriched ester 3a and alcohol 3b (e.e. ≥92%). Treatment of 3a and 3b with NH4OH/MeOH afforded the corresponding β-lactams (1R,8S)-2a and (1S,8R)-2b (e.e. ≥93%), potential starting compounds in anatoxin-a synthesis. The ring opening of lactams (±)-2, (±)-7, 3a and 3b, followed by reduction, resulted in racemic 4-6 and 8 and enantiomeric 4a, 4b, 5a and 5b eight-membered cyclic β-amino acid derivatives.
Efficient enzymatic routes for the synthesis of new eight-membered cyclic β-amino acid and β-lactam enantiomers
Forró, Eniko,Kiss, Loránd,árva, Judit,Fül?p, Ferenc
, (2018/01/17)
Efficient enzymatic resolutions are reported for the preparation of new eight-membered ring-fused enantiomeric β-amino acids [(1R, 2S)-9 and (1S, 2R)-9] and β-lactams [(1S, 8R)-3, (1R, 8S)-3 (1S, 8R)-4 and (1R, 8S)-7], through asymmetric acylation of (±)-4 (E > 100) or enantioselective hydrolysis (E > 200) of the corresponding inactivated (±)-3 or activated (±)-4 β-lactams, catalyzed by PSIM or CAL-B in an organic solvent. CAL-B-catalyzed ring cleavage of (±)-6 (E > 200) resulted in the unreacted (1S, 8R)-6, potential intermediate for the synthesis of enantiomeric anatoxin-a. The best strategies, in view of E, reaction rate and product yields, which underline the importance of substrate engineering, are highlighted.
Synthesis of mono- and dihydroxy-substituted 2-aminocyclooctanecarboxylic acid enantiomers
Palko, Marta,Benedek, Gabriella,Forro, Enik,Weber, Edit,Haenninen, Mikko,Sillanpaeae, Reijo,Fueloep, Ferenc
experimental part, p. 957 - 961 (2010/08/06)
(1R,2S,6R)-2-Amino-6-hydroxycyclooctanecarboxylic acid (-)-10 was synthesized from (1R,2S)-2-aminocyclooct-5-enecarboxylic acid (+)-2 via an iodolactone intermediate, while (1R,2S,3R,4S)-2-amino-5,6- dihydroxycyclooctanecarboxylic acid (-)-12 was prepared
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
