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The Role of Silyl Protecting Group for the Synthesis of Procyanidins and Their Derivatives

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New Horizons of Process Chemistry

Abstract

The intramolecular [4–8] coupling of silyl-protected catechin and epicatechins is examined. Coupling reaction of silyl-protected epicatechin/catechin, epicatechin/epicatechin, catechin/catechin and catechin/epicatechin worked well to afford the corresponding dimers with excellent selectivity and yield. The series of procyanidin B analogues synthesis are achieved. We also carried out the synthesis of 3-O- and/or 5-O-acyl-catechin and epicatechin derivatives on a gram scale.

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Authors and Affiliations

  1. Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama, 939-0398, Japan

    Noriyuki Nakajima

  2. Graduate School of Engineering, Osaka Electro-communication University (OECU), 18-8 Hatsu-cho, Neyagawa-shi, Osaka, 572-8530, Japan

    Akiko Saito

Authors
  1. Noriyuki Nakajima
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  2. Akiko Saito
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Correspondence to Noriyuki Nakajima .

Editor information

Editors and Affiliations

  1. Doshisha Women's College of Liberal Arts , Kyotanabe, Japan

    Kiyoshi Tomioka

  2. Meijo University, Nagoya, Japan

    Takayuki Shioiri

  3. Gifu Pharmaceutical University , Gifu, Japan

    Hironao Sajiki

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Nakajima, N., Saito, A. (2017). The Role of Silyl Protecting Group for the Synthesis of Procyanidins and Their Derivatives. In: Tomioka, K., Shioiri, T., Sajiki, H. (eds) New Horizons of Process Chemistry. Springer, Singapore. https://doi.org/10.1007/978-981-10-3421-3_17

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