Synlett 2019; 30(02): 189-192
DOI: 10.1055/s-0037-1611361
letter
© Georg Thieme Verlag Stuttgart · New York

Highly Selective One-Pot Synthesis of Polysubstituted Isoflavanes using Styryl Ethers and Electron-Withdrawing ortho-Quinone Methides Generated In Situ

,
Mami Kishimoto
,
Naoya Ohtsuka
,
Yoshinori Iwama
,
Hiroki Wada
,
Graduate School of Environment and Information Sciences, Yokohama National University, Tokiwadai, Hodogaya-ku, Yokohama 240-8501, Japan   Email: honda-kiyoshi-rb@ynu.ac.jp   Email: hoshino-yujiro-hy@ynu.ac.jp
,
Kiyoshi Honda*
Graduate School of Environment and Information Sciences, Yokohama National University, Tokiwadai, Hodogaya-ku, Yokohama 240-8501, Japan   Email: honda-kiyoshi-rb@ynu.ac.jp   Email: hoshino-yujiro-hy@ynu.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 13 September 2018

Accepted after revision: 25 October 2018

Publication Date:
17 December 2018 (online)

Abstract

A highly selective one-pot synthesis of polysubstituted isoflavanes has been developed. The reaction proceeds through the cycloaddition of methyl styryl ethers, derived from phenylacetaldehyde dimethyl acetals under acidic conditions, with electron-withdrawing ortho-quinone methides generated in situ. When phenylacetaldehyde dimethyl acetals were reacted with salicylaldehydes, the reaction proceeded smoothly to afford the corresponding isoflavanes stereoselectively in high yields and with excellent regioselectivities. The present reaction provides versatile access to functionalized isoflavanes, and constitutes a useful tool for the synthesis of biologically active molecules.

Supporting Information

 
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