In this work, we describe the synthesis of (±)-permethylated-ϵ-viniferin from resveratrol by successive iodination, methylation and dehalogenation reactions. Iodination reaction by N-iodosuccinimide (NIS) was studied to optimize and confirm a proposed radical mechanism. Switching to acetyl protecting group, a new straightforward regio- and diastereo-selective biomimetic synthesis of (±)-ϵ-viniferin was obtained. Permethylated and free ϵ-viniferin were isolated up to 20 %yield.

Regio- and Diastereo-Selective Biomimetic Synthesis of (+/-)-ε-Viniferin by NIS and Resveratrol

Paolo Lupattelli;
2021

Abstract

In this work, we describe the synthesis of (±)-permethylated-ϵ-viniferin from resveratrol by successive iodination, methylation and dehalogenation reactions. Iodination reaction by N-iodosuccinimide (NIS) was studied to optimize and confirm a proposed radical mechanism. Switching to acetyl protecting group, a new straightforward regio- and diastereo-selective biomimetic synthesis of (±)-ϵ-viniferin was obtained. Permethylated and free ϵ-viniferin were isolated up to 20 %yield.
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Note: https://doi.org/10.1002/slct.202101678
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11573/1653062
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