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Regio‐ and Diastereo‐Selective Biomimetic Synthesis of (±)‐ ϵ ‐Viniferin by NIS and Resveratrol
Author(s) -
D'Orsi Rosarita,
Morrongiello Francesca,
Laurita Teresa,
Funicello Maria,
Lupattelli Paolo,
Chiummiento Lucia
Publication year - 2021
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202101678
Subject(s) - halogenation , chemistry , resveratrol , yield (engineering) , methylation , combinatorial chemistry , organic chemistry , biochemistry , materials science , gene , metallurgy
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.