Asymmetric Biomimetic Oxidations of Phenols: The Mechanism of the Diastereo- and Enantioselective Synthesis of Thomasidioic Acid

doi:10.3390/molecules13010129

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Molecules 2008, 13(1), 129-148; doi:10.3390/molecules13010129

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Asymmetric Biomimetic Oxidations of Phenols: The Mechanism of the Diastereo- and Enantioselective Synthesis of Thomasidioic Acid

Luca Zoia , Maurizio Bruschi , Marco Orlandi * , Eeva-Liisa Tolppa and Bruno Rindone

Department of Environmental Sciences, University of Milan, Piazza della Scienza, 1, 20126 Milan, Italy

* Author to whom correspondence should be addressed.

Received: 26 November 2007; in revised form: 21 January 2008 / Accepted: 21 January 2008 / Published: 23 January 2008

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Abstract: Enantiopure chiral amidic derivatives of sinapic acid were oxidised withhydrogen peroxide using horseradish peroxidase (HRP) as the catalyst to give thearyltetraline dilignol thomasidioic acid. Trans-diastereoselectivity and enantioselectivity inthe formation of thomasidioic acid was observed. Computational methods show that theenantioselectivity is controlled by the β-β oxidative coupling step, while thediastereoselectivity is controlled by the stability of the reactive conformation of theintermediate quinomethide.

Keywords: Diastereoselection; enantioselection; lignans; horseradish peroxidase; oxidative

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MDPI and ACS Style

Zoia, L.; Bruschi, M.; Orlandi, M.; Tolppa, E.-L.; Rindone, B. Asymmetric Biomimetic Oxidations of Phenols: The Mechanism of the Diastereo- and Enantioselective Synthesis of Thomasidioic Acid. Molecules 2008, 13, 129-148.

AMA Style

Zoia L., Bruschi M., Orlandi M., Tolppa E.-L., Rindone B. Asymmetric Biomimetic Oxidations of Phenols: The Mechanism of the Diastereo- and Enantioselective Synthesis of Thomasidioic Acid. Molecules. 2008; 13(1):129-148.

Chicago/Turabian Style

Zoia, Luca; Bruschi, Maurizio; Orlandi, Marco; Tolppa, Eeva-Liisa; Rindone, Bruno. 2008. "Asymmetric Biomimetic Oxidations of Phenols: The Mechanism of the Diastereo- and Enantioselective Synthesis of Thomasidioic Acid." Molecules 13, no. 1: 129-148.

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