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 / D'Orsi, Rosarita; Morrongiello, Francesca; Laurita, Teresa; Funicello, Maria; Lupattelli, Paolo; Chiummiento, Lucia. - In: CHEMISTRYSELECT. - ISSN 2365-6549. - 6:27(2021), pp. 6863-6866. [10.1002/slct.202101678]
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.| File | Dimensione | Formato | |
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