Solvent‐Controlled Hydrogenation of 2’‐Hydroxychalcones: A Simple Solution to the Total Synthesis of Bussealins,Advanced Synthesis & Catalysis

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Solvent‐Controlled Hydrogenation of 2’‐Hydroxychalcones: A Simple Solution to the Total Synthesis of Bussealins
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2020-09-16 , DOI: 10.1002/adsc.202000892
Martín Soto ₁ , Raquel G. Soengas ₁ , Humberto Rodríguez‐Solla ₁

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A solvent‐controlled hydrogenation of 2’‐hydroxychalcones to selectively obtain different hydrogenation products is herein reported. Thus, hydrogenation of 2’‐hydroxychalcones using EtOH as solvent provided the corresponding 1,3‐diarylpropanes in excellent yields. On the contrary, when the hydrogenation was performed in DCM, the corresponding dihydrochalcones were isolated. Switching the reaction solvent to n‐BuOH/H₂O (1:1), afforded 1,3‐diarylpropanols from moderate to good yields. The methodology here reported offers a straightforward, simple and cost‐effective method for the preparation of a wide variety of 2’‐hydroxy‐1,3‐diarylpropanes derivatives, and was also applied to the preparation of natural Bussealins C and D.

中文翻译：

溶剂控制的2'-羟基查耳酮的氢化反应：简单合成Bussealins的简单方法

本文报道了溶剂控制的2'-羟基查耳酮氢化，以选择性地获得不同的氢化产物。因此，使用EtOH作为溶剂对2'-羟基查耳酮进行氢化，可以以优异的产率提供相应的1,3-二芳基丙烷。相反，当在DCM中进行氢化时，分离出相应的二氢查耳酮。将反应溶剂切换为n- BuOH / H ₂ O（1：1），得到1,3-二芳基丙醇，产率从中等到良好。此处报道的方法为制备各种2'-羟基-1,3-二芳基丙烷衍生物提供了一种简单，简单且具有成本效益的方法，并且还应用于天然Bussealins C和D的制备。

更新日期：2020-09-16

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