Issue 32, 2015
From the journal:

Chemical Communications

The flavan–isoflavan rearrangement: bioinspired synthetic access to isoflavonoids via 1,2-shift–alkylation sequence†

Kayo Nakamura,a   Ken Ohmori*a  and  Keisuke Suzuki*a  

* Corresponding authors

a Department of Chemistry, Tokyo Institute of Technology, O-okayama, Meguro, Tokyo 152-8551, Japan
E-mail: kohmori@chem.titech.ac.jp, ksuzuki@chem.titech.ac.jp

Abstract

An approach to 2-substituted isoflavonoids is reported based on the 1,2-shift of the aryl group in the catechin skeleton followed by the in situ alkylation. Synthesis of (−)-equol, a natural isoflavan with estrogenic activities, was achieved.

Graphical abstract: The flavan–isoflavan rearrangement: bioinspired synthetic access to isoflavonoids via 1,2-shift–alkylation sequence

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Article information

DOI
https://doi.org/10.1039/C5CC01572C
Article type
Communication
Submitted
21 Feb 2015
Accepted
16 Mar 2015
First published
24 Mar 2015

Chem. Commun., 2015,51, 7012-7014

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The flavan–isoflavan rearrangement: bioinspired synthetic access to isoflavonoids via 1,2-shift–alkylation sequence

K. Nakamura, K. Ohmori and K. Suzuki, Chem. Commun., 2015, 51, 7012 DOI: 10.1039/C5CC01572C

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