STUDIES ON THE DIASTEREO- SELECTIVE REDUCTION OF 2-Acetyl-2-Alkyl- Γ-Butyrolactones WITH BORON HYDRIDES*

Teixeira, Lis H. P.; Souza, Maria Cecília B. V. de; Ramos, Mônica Freiman de Souza; Neto, Francisco Radler de Aquino; Barreiro, Eliezer J.; Fraga, Carlos A.M.

doi:10.1081/scc-120002396

Cited by 10 publications

(8 citation statements)

References 19 publications

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“…Our investigation started off with the chemical reduction of α-acetylbutyrolactone 1 by NaBH 4 . The reaction was carried out according to the procedure worked out by Teixeira et al [17] and we derived anti-to-syn isomers of α'-1'-hydroxyethyl-γ-butyrolactone 2 in a ratio of 1:7 (Figure 1), which were used as GC standards for product 2. . After a suitable period of time, the medium (20 mL) containing unreacted substrate, product and mycelium was extracted with ethyl acetate (20 mL).…”

Section: Resultsmentioning

confidence: 99%

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Yeast-Mediated Stereoselective Reduction of α-Acetylbutyrolactone

et al. 2018

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α’-1’-Hydroxyethyl-γ-butyrolactone—a product of reduction of α-acetylbutyrolactone possesses two stereogenic centres and two reactive functionalities (an alcohol and an ester group). Additionally, this compound has a similar structure to γ-butyrolactone (GBL) which is psychoactive. In the present work, biotransformation using seven yeast strains was used to obtain anti stereoisomers of α’-1’-hydroxyethyl-γ-butyrolactone. The process was carried out in both growing and resting culture. The effect of media composition and organic solvent addition on stereoselectivity and effectiveness of biotransformation was also studied. After one day of transformation, optically pure (3R,1’R)-hydroxylactone was obtained by means of Yarrowia lipolytica P26A in YPG medium (yeast extract (1%), peptone (2%) and glucose (2%)). In turn, the use of resting cells culture of Candida viswanathi AM120 in the presence of 10% DES (deep eutectic solvent) allowed us to obtain a (3S,1’S)-enantiomer with de = 85% (diastereomeric excess) and ee 76% (enantiomeric excess).

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Section: Resultsmentioning

confidence: 99%

“…The chemical reduction of α-acetylbutyrolactone 1 was carried out according to the procedure worked out by Teixeira et al [17]. α-Acetylbutyrolactone 1 (1 g, 7.8 mmol) in 30 mL of methanol was stirred 30 min in room temperature in the presence of CaCl 2 (1.73 g, 15.6 mmol).…”

Section: Synthesis Of Standardsmentioning

confidence: 99%

Yeast-Mediated Stereoselective Reduction of α-Acetylbutyrolactone

et al. 2018

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“…The reaction was carried out according to the procedure worked out by Teixeira et al [12]. As result of this chemical reaction we received anti -to- syn isomers of α’-1′-hydroxyethyl-γ-butyrolactone 2 in a ratio of 1:7.…”

Section: Resultsmentioning

confidence: 99%

“…The chemical reduction of α-acetylbutyrolactone 1 was carried out according to the procedure worked out by Teixeira et al [12]. α-Acetylbutyrolactone 1 (1 g, 7.8 mmol) in 30 mL of methanol was stirred for 30 min at room temperature in the presence of CaCl 2 (1.73 g, 15.6 mmol).…”

Section: Methodsmentioning

confidence: 99%

“…This compound is a structural analog of γ-butyrolactone (GLB) which exerts several inhibitory actions over CNS through interaction with specific neuronal high-affinity receptors [11]. Additionally, because it is a bifunctional compound (lactone and alcohol), it could be a useful building block in asymmetric synthesis [12]. In biological tests it is essential to use compounds in their pure enantiomer forms, especially when synthesizing pharmaceuticals, where a high enantiomeric excess is required to prevent undesired side effects by the second enantiomer [13].…”

Section: Introductionmentioning

confidence: 99%

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Biotransformation of α-Acetylbutyrolactone in Rhodotorula Strains

Mączka

Wińska

Grabarczyk

et al. 2018

IJMS

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Due to its structural similarity, the α’-1′-hydroxyethyl-γ-butyrolactone obtained by reduction of (±)-α-acetyl-γ-butyrolactone may have a similar function in the body to γ-butyrolactone (GBL). In the work presented, biotransformation of α-acetyl-γ-butyrolactone by three Rhodotorula strains was performed obtaining enantiomerically enriched alcohol. The process was carried out in growing and resting cultures. We studied how both media composition and organic solvent volume affected stereoselectivity and effectiveness of biotransformation. After 2 h, the enantiomerically pure (3R, 1′S)-α’-1′-hydroxyethyl-γ-butyrolactone was obtained using the R. marina AM77 strain in YPG (Yeast extract-Peptone-Glucose) medium enriched with 5% glycerol. To our best knowledge there is no previous information in the literature about the (±)-α-acetyl-γ-butyrolactone biotransformation performed in medium with addition of organic and deep eutectic solvents.

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ChemInform Abstract: Studies on the Diastereoselective Reduction of 2‐Acetyl‐2‐alkyl‐γ‐butyrolactones with Boron Hydrides.

Teixeira¹,

Souza²,

Ramos³

et al. 2002

ChemInform

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diastereoselective syntheses, enantioselective syntheses diastereoselective syntheses, enantioselective syntheses (incl. cis/trans-isomerism) O 0031 -047Studies on the Diastereoselective Reduction of 2-Acetyl-2-alkyl-γbutyrolactones with Boron Hydrides.-The diastereoselectivity of borohydride reduction of the title butyrolactones under varying reaction conditions (i.e. presence or absence of chelating agents) is studied in detail.The results indicate that the diastereoselectivity is more dependent on steric interactions than on chelation factors. -(TEIXEIRA, LIS H. P.; DE SOUZA, MARIA CECILIA B. V.; RAMOS, MARIA DA CONCEICAO K. V.; DE AQUINO NETO, FRANCISCO R.; BARREIRO, ELIEZER J.; FRAGA, CARLOS A. M.; Synth. Commun. 32 (2002) 4, 505-526; Lab. Avaliacao Sint. Subst. Bioativas, Fac. Farm., Univ. Fed. Rio de Janeiro,

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STUDIES ON THE DIASTEREO- SELECTIVE REDUCTION OF 2-Acetyl-2-Alkyl- Γ-Butyrolactones WITH BORON HYDRIDES*

Cited by 10 publications

References 19 publications

Yeast-Mediated Stereoselective Reduction of α-Acetylbutyrolactone

Yeast-Mediated Stereoselective Reduction of α-Acetylbutyrolactone

Biotransformation of α-Acetylbutyrolactone in Rhodotorula Strains

ChemInform Abstract: Studies on the Diastereoselective Reduction of 2‐Acetyl‐2‐alkyl‐γ‐butyrolactones with Boron Hydrides.

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