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Molecules 2018, 23(7), 1653; https://doi.org/10.3390/molecules23071653

General Method for the Synthesis of (−)-Conduritol C and Analogs from Chiral Cyclohexadienediol Scaffolds

1
Laboratorio de Síntesis Orgánica, Departamento de Química Orgánica, Facultad de Química, Av. Gral. Flores 2124, Universidad de la República, Montevideo CP11800, Uruguay
2
Cryssmat-Lab/DETEMA, Facultad de Química, Av. Gral. Flores 2124, Universidad de la República, Montevideo CP11800, Uruguay
3
Department of Chemistry, Universidad de los Andes, Carrera 1 N8 18 A-12, Bogotá 111711, Colombia
*
Author to whom correspondence should be addressed.
Academic Editors: Laura Palombi, Antonio Massa and Derek J. McPhee
Received: 31 May 2018 / Revised: 29 June 2018 / Accepted: 1 July 2018 / Published: 6 July 2018
(This article belongs to the Special Issue Enantioselective Catalysis)
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Abstract

An efficient and facile general method for the synthesis of conduritol C analogs, taking advantage of an enantioselective biocatalysis process of monosubstituted benzenes, is described. The absolute stereochemical patterns of the target molecules (−)-conduritol C, (−)-bromo-conduritol C, and (−)-methyl-conduritol C were achieved by means of chemoenzymatic methods. The stereochemistry present at the homochiral cyclohexadiene-cis-1,2-diols derived from the arene biotransformation and the enantioselective ring opening of a non-isolated vinylepoxide derivative permitted the absolute configuration of the carbon bearing the hydroxyl groups at the target molecules to be established. All three conduritols and two intermediates were crystallized, and their structures were confirmed by X-ray diffraction. The three conduritols and intermediates were isostructural. The versatility of our methodology is noteworthy to expand the preparation of conduritol C analogs starting from toluene dioxygenase (TDO) monosubstituted arene substrates. View Full-Text
Keywords: conduritol C; enantioselective biocatalysis; arene biotransformation; crystal structures; α-glycosidase inhibitors conduritol C; enantioselective biocatalysis; arene biotransformation; crystal structures; α-glycosidase inhibitors
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Tibhe, G.D.; Macías, M.A.; Schapiro, V.; Suescun, L.; Pandolfi, E. General Method for the Synthesis of (−)-Conduritol C and Analogs from Chiral Cyclohexadienediol Scaffolds. Molecules 2018, 23, 1653.

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