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Synthesis 2010(22): 3822-3826  
DOI: 10.1055/s-0030-1258242
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Regioselective FeCl3-Promoted Biomimetic Synthesis of Dimeric Isorhapontigenin

Wenling Li*a,b, Yaling Luoa, Hongfu Lia, Peng Zanga, Xiaoqian Hana
a School of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, P. R. of China
b State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
Fax: +86(931)4956512; e-Mail: liwl@mail.lzjtu.cn;
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Publication History

Received 21 June 2010
Publication Date:
03 September 2010 (online)

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Abstract

An efficient approach to the preparation of natural (±)-gneafricanin F and the first synthesis of (±)-gnemonol M were developed. The regioselective, oxidative coupling of 5-tert-butylisorhapontigenin catalyzed by FeCl3˙6H2O in different solvent systems was used as the key synthetic step.

Key words

isorhapontigenin - gneafricanin F - gnemonol M - biomimetic synthesis - oxidative coupling

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