Synthesis of a New (+)-Catechin-Derived Compound: 8-Vinylcatechin

Luis      Cruz; Enrique      Borges; Artur   M.S.   Silva; Nuno      Mateus; Victor      de Freitas

doi:10.2174/157017808785982211

Abstract

A strategy for the synthesis of 8-vinylcatechin was developed, which involves (+)-catechin silylation with TBDMS-Cl, followed by bromination with NBS, a cross-coupling Suzuki reaction with vinylboronic acid pinacol ester and cleavage of TBDMS groups with TBAF, affording the 8-vinylcatechin.

Keywords: (+)-Catechin, silylation, bromination, Suzuki coupling, desilylation, 8-vinylcatechin

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Letters in Organic Chemistry

Title: Synthesis of a New (+)-Catechin-Derived Compound: 8-Vinylcatechin

Volume: 5 Issue: 7

Author(s): Luis Cruz, Enrique Borges, Artur M.S. Silva, Nuno Mateus and Victor de Freitas

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Keywords: (+)-Catechin, silylation, bromination, Suzuki coupling, desilylation, 8-vinylcatechin

Abstract: A strategy for the synthesis of 8-vinylcatechin was developed, which involves (+)-catechin silylation with TBDMS-Cl, followed by bromination with NBS, a cross-coupling Suzuki reaction with vinylboronic acid pinacol ester and cleavage of TBDMS groups with TBAF, affording the 8-vinylcatechin.

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Cruz Luis, Borges Enrique, Silva M.S. Artur, Mateus Nuno and de Freitas Victor, Synthesis of a New (+)-Catechin-Derived Compound: 8-Vinylcatechin, Letters in Organic Chemistry 2008; 5 (7) . https://dx.doi.org/10.2174/157017808785982211