Enzyme-Triggered Enantioconvergent Transformation of Haloalkyl Epoxides

Mayer, Sandra F.; Steinreiber, Andreas; Orru, Romano V. A.; Faber, Kurt

doi:10.1002/1099-0690(200112)2001:23<4537::aid-ejoc4537>3.3.co;2-5

Cited by 4 publications

(7 citation statements)

References 5 publications

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“…This latter reaction shows some resemblance to a Payne-type rearrangement ,, Due to the enantioconvergence, chemical yields were markedly beyond the 50% limitation set for kinetic resolutions. Such ‘deracemization' processes have recently gained considerably attention due to their improved economic balance …”

Section: Introductionmentioning

confidence: 94%

Chemoenzymatic Asymmetric Total Syntheses of Antitumor Agents (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and (R)- and (S)-Falcarinol from Panax ginseng Using an Enantioconvergent Enzyme-Triggered Cascade Reaction

Mayer

Steinreiber

Orru³

et al. 2002

J. Org. Chem.

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108

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Total asymmetric synthesis of two components of Panax ginseng showing antitumor activity, i.e., (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and of both enantiomers of Falcarinol was accomplished. Due to the fact that the synthetic strategy was based on enantioconvergent biotransformations, the occurrence of any undesired stereoisomer was entirely avoided. The absolute configuration of naturally occurring Panaxytriol was confirmed to be (3R,9R,10R) on the basis of optical rotation values. It was shown that enzyme-triggered cascade reactions represent a valuable tool for the synthesis of natural products.

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Section: Introductionmentioning

confidence: 94%

Chemoenzymatic Asymmetric Total Syntheses of Antitumor Agents (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and (R)- and (S)-Falcarinol from Panax ginseng Using an Enantioconvergent Enzyme-Triggered Cascade Reaction

Mayer

Steinreiber

Orru³

et al. 2002

J. Org. Chem.

Self Cite

108

View full text Add to dashboard Cite

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“…9 Analytical data are consistent with the literature. 10 (E)-Dec-2-en-1-yl Acetate (8d). This commercially available compound was prepared according to the literature procedure.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…Analytical data are consistent with the literature. 15 (E)-Hex-3-en-1-yl Benzoate (10). This compound was prepared by the general procedure for benzoyl protection using 1.56 g of (E)dec-2-en-1-ol.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Wacker-Type Oxidation of Internal Alkenes using Pd(Quinox) and TBHP

et al. 2013

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The Pd-catalyzed TBHP-mediated Wacker-type oxidation of internal alkenes is reported. The reaction uses 2-(4,5-dihydro-2-oxazolyl)quinoline (Quinox) as ligand and TBHP(aq) as oxidant to deliver single ketone constitutional isomer products in a predictable fashion from electronically-biased olefins. This methodology is showcased through its application on an advanced intermediate in the total synthesis of the anti-malarial drug, artemisinin.

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“…out in Tris buffer (pH 8) with lyophilized cells from a selection of microorganisms possessing epoxide hydrolase activity. 110 Similarly, the enzyme-mediated synthesis of two isomers of naturally occurring pheromone pityol was designed based on retrosynthetic analysis, which identified a brominated epoxide as a possible precursor. This compound with fixed absolute configuration for the carbon bearing the halogen was used as a mixture of isomeric epoxides and subjected to diastereoconvergent hydrolysis by epoxide hydrolase contained in whole cells of Rhodococcus ruber DSM 44540.…”

Section: Spontaneous Cascades Triggered By a Single Enzymementioning

confidence: 99%

Artificial Biocatalytic Linear Cascades for Preparation of Organic Molecules

et al. 2017

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The review compiles artificial cascades involving enzymes with a focus on the last 10 years. A cascade is defined as the combination of at least two reaction steps in a single reaction vessel without isolation of the intermediates, whereby at least one step is catalyzed by an enzyme. Additionally, cascades performed in vivo and in vitro are discussed separately, whereby in vivo cascades are defined here as cascades relying on cofactor recycling by the metabolism or on a metabolite from the living organism. The review introduces a systematic classification of the cascades according to the number of enzymes in the linear sequence and differentiates between cascades involving exclusively enzymes and combinations of enzymes with non-natural catalysts or chemical steps. Since the number of examples involving two enzymes is predominant, the two enzyme cascades are further subdivided according to the number, order, and type of redox steps. Furthermore, this classification differentiates between cascades where all reaction steps are performed simultaneously, sequentially, or in flow.

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Enzyme-Triggered Enantioconvergent Transformation of Haloalkyl Epoxides

Cited by 4 publications

References 5 publications

Chemoenzymatic Asymmetric Total Syntheses of Antitumor Agents (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and (R)- and (S)-Falcarinol from Panax ginseng Using an Enantioconvergent Enzyme-Triggered Cascade Reaction

Chemoenzymatic Asymmetric Total Syntheses of Antitumor Agents (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and (R)- and (S)-Falcarinol from Panax ginseng Using an Enantioconvergent Enzyme-Triggered Cascade Reaction

Wacker-Type Oxidation of Internal Alkenes using Pd(Quinox) and TBHP

Artificial Biocatalytic Linear Cascades for Preparation of Organic Molecules

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