Selective Synthesis of Epicatechin Dimers By Zinc(II) Triflate Mediated Self-Condensation

Manato Suda; Wataru Fujii; Kohki Takanashi; Yasunao Hattori; Hidefumi Makabe

doi:10.1055/s-0034-1378998

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(24): 3351-3355
DOI: 10.1055/s-0034-1378998

paper

Selective Synthesis of Epicatechin Dimers By Zinc(II) Triflate Mediated Self-Condensation

Manato Suda

^aGraduate School of Agriculture, Sciences of Functional Foods, Shinshu University, 8304 Minami-minowa, Kami-ina, Nagano, 399-4598, Japan Fax: +81(265)771700 eMail: makabeh@shinshu-u.ac.jp

,

Wataru Fujii

^aGraduate School of Agriculture, Sciences of Functional Foods, Shinshu University, 8304 Minami-minowa, Kami-ina, Nagano, 399-4598, Japan Fax: +81(265)771700 eMail: makabeh@shinshu-u.ac.jp

,

Kohki Takanashi

^aGraduate School of Agriculture, Sciences of Functional Foods, Shinshu University, 8304 Minami-minowa, Kami-ina, Nagano, 399-4598, Japan Fax: +81(265)771700 eMail: makabeh@shinshu-u.ac.jp

,

Yasunao Hattori

^bDepartment of Medicinal Chemistry, Kyoto Pharmaceutical University, Yamashina-ku, Kyoto 607-8412, Japan

,

Hidefumi Makabe*

^aGraduate School of Agriculture, Sciences of Functional Foods, Shinshu University, 8304 Minami-minowa, Kami-ina, Nagano, 399-4598, Japan Fax: +81(265)771700 eMail: makabeh@shinshu-u.ac.jp

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Abstract

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Abstract

Epicatechin dimers were synthesized by zinc(II) triflate mediated self-condensation reactions of epicatechin monomer derivatives. One synthesized dimer was successfully converted into procyanidin C1.

Key words

phenols - Lewis acids - oligomerization - natural products - stereoselective synthesis

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Referenzen

References
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14 HPLC measurement conditions: column, Inertsil ODS-3, 250 × 4.6 mm GL-Sciences; eluent: MeOH–0.2% AcOH (5:95 to 25:75), flow rate: 0.8 mL/min; detection: UV, λ = 280 nm; retention time: 23.60 min.

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