Synthesis of enantiomerically pure (S)- and (R)-fluoxetine (Prozac®) via a hetero Diels–Alder strategy

Panunzio, Mauro; Rossi, K.; Tamanini, Emiliano; Campana, Eileen; Martelli, Gianluca

doi:10.1016/j.tetasy.2004.09.009

Cited by 20 publications

(5 citation statements)

References 16 publications

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“…It may also be possible to use a fluoride sensor in combination with an enzyme to quantify specific compounds [18]. Additionally, antidepressant pharmaceuticals such as (R)-fluoxetine (prozac) contain C À F bonds [19], and sensitive fluoride detection could assist in more fully elucidating the metabolic pathway of these compounds.…”

Section: Introductionmentioning

confidence: 99%

Aluminum(III) Porphyrins as Ionophores for Fluoride Selective Polymeric Membrane Electrodes

et al. 2006

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Aluminum(III) porphyrins are examined as potential fluoride selective ionophores in polymeric membrane type ionselective electrodes. Membranes formulated with Al(III) tetraphenyl (TPP) or octaethyl (OEP) porphyrins are shown to exhibit enhanced potentiometric selectivity for fluoride over more lipophilic anions, including perchlorate and thiocyanate. However, such membrane electrodes display undesirable super-Nernstian behavior, with concomitant slow response and recovery times. By employing a sterically hindered Al(III) picket fence porphyrin (PFP) complex as the membrane active species, fully reversible and Nernstian response toward fluoride is achieved. This finding suggests that the super-Nernstian behavior observed with the nonpicket fence metalloporphyrins is due to the formation of aggregate porphyrin species (likely dimers) within the membrane phase. The steric hindrance of the PFP ligand structure eliminates such chemistry, thus leading to theoretical response slopes toward fluoride. Addition of lipophilic anionic sites into the organic membranes enhances response and selectivity, indicating that the Al(III) porphyrin ionophores function as charged carrier type ionophores. Optimized membranes formulated with Al(III)-PFP in an o-nitrophenyloctyl ether plasticized PVC film exhibit fast response to fluoride down to 40 mM, with very high selectivity over SCN, Br À and NO 3 À (k pot < 10 À3 for all anions tested). With further refinements in the membrane chemistry, it is anticipated that Al(III) porphyrin-based membrane electrodes can exhibit potentiometric fluoride response and selectivity that approaches that of the classical solid-state LaF 3 crystal-based fluoride sensor.

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Section: Introductionmentioning

confidence: 99%

Aluminum(III) Porphyrins as Ionophores for Fluoride Selective Polymeric Membrane Electrodes

et al. 2006

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“…Chiral secondary alcohols are good examples of chiral compounds that can be used in the production of different drugs. For instance, isoproterenol which is used for the treatment of bradycardia, prozac which is used in the treatment of depression and neobenodine which display antihistaminic and anticholinergic action are synthesized from chiral secondary alcohols ( Fig. ).…”

Section: Introductionmentioning

confidence: 99%

Highly Enantioselective Production of Chiral Secondary Alcohols with Candida zeylanoides as a New Whole Cell Biocatalyst

Şahin

Dertli

2017

Chemistry & Biodiversity

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The increasing demand for biocatalysts in synthesizing enantiomerically pure chiral alcohols results from the outstanding characteristics of biocatalysts in reaction, economic, and ecological issues. Herein, fifteen yeast strains belonging to three food originated yeast species Candida zeylanoides, Pichia fermentans, and Saccharomyces uvarum were tested for their capability for asymmetric reduction of acetophenone to 1-phenylethanol as biocatalysts. Of these strains, C. zeylanoides P1 showed an effective asymmetric reduction ability. Under optimized conditions, substituted acetophenones were converted to corresponding optically active secondary alcohols in up to 99% enantiomeric excess and at high yields. The preparative scale asymmetric bioreduction of 4-nitroacetophenone (1m) by C. zeylanoides P1 gave (S)-1-(4-nitrophenyl)ethanol (2m) with 89% yield and > 99% enantiomeric excess. Compound 2m has been obtained in an enantiomerically pure and inexpensive form. Additionally, these results indicate that C. zeylanoides P1 is a promising biocatalyst for the synthesis of chiral alcohols in industry.

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“…No Comments on Table 1 a) Although the formation of the cycloadducts 2 and 3 takes place even under classical heating conditions (CH, 21,22 in all cases, immaterial of the final goal of the production of 1,3-aminols, scaffolds of CNS drugs like Prozac ® , and its congeners.…”

Section: Psp 89mentioning

confidence: 99%

“…It was gratifying to find out that the above reported procedure must be considered efficient and valuable in view of the possibility to build up a small library of oxazinan-2-ones, which may in turn, be elaborated to a 1,3-aminols according to already published protocols. 21,22 Hetero-Diels-Alder Reaction of Azadienes 1, 4 with Aromatic Aldehydes; trans-2,6-Diphenyl [1,3] AcCl (0.430 mL, 6 mmol) in hexane (2 mL), and the mixture was stirred for 2 h at r.t. The mixture was filtered through a Celite pad and the solvent was evaporated.…”

Section: Psp 89mentioning

confidence: 99%

“…[17][18][19][20] The HDA-cycloadducts thus obtained have been demonstrated to serve as useful intermediates for the preparation of 1,3-aminols, scaffolds of a wide range of biologically active compounds including CNS drugs as Prozac ® . 21,22 The synthesis of the target compounds was extensively optimized using azadiene 1 and benzaldehyde as test sub-strata (Scheme 1 and Table 1). As underlined in Table 1, entry 5, the best conversion of azadiene 1 into HDA adduct was achieved in chlorobenzene as solvent and Eu-FOD as lanthanide catalyst.…”

Section: Introductionmentioning

confidence: 99%

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EuFOD-Catalyzed Hetero-Diels-Alder (HDA) Reaction under Microwave Heating

Panunzio¹,

Bandini²,

D'Aurizio³

et al. 2007

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Synthesis of enantiomerically pure (S)- and (R)-fluoxetine (Prozac®) via a hetero Diels–Alder strategy

Cited by 20 publications

References 16 publications

Aluminum(III) Porphyrins as Ionophores for Fluoride Selective Polymeric Membrane Electrodes

Aluminum(III) Porphyrins as Ionophores for Fluoride Selective Polymeric Membrane Electrodes

Highly Enantioselective Production of Chiral Secondary Alcohols with Candida zeylanoides as a New Whole Cell Biocatalyst

EuFOD-Catalyzed Hetero-Diels-Alder (HDA) Reaction under Microwave Heating

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