Synthesis of resveratrol tetramers via a stereoconvergent radical equilibrium

Abstract

Persistent free radicals have become indispensable in the synthesis of organic materials by living radical polymerization. However, examples of their use in the synthesis of small molecules are rare. Herein, we report the application of persistent radical and quinone methide intermediates to the synthesis of the resveratrol tetramers nepalensinol B and vateriaphenol C. The spontaneous cleavage and reconstitution of exceptionally weak carbon-carbon bonds has enabled a stereoconvergent oxidative dimerization of racemic materials in a transformation that likely coincides with the biogenesis of these natural products. The efficient synthesis of higher-order oligomers of resveratrol will facilitate the biological studies necessary to elucidate their mechanism(s) of action.

Gnetin‐C and other resveratrol oligomers with cancer chemopreventive potential

“…To enhance the bioavailability and cytotoxic activity of resveratrol and its oligomers, a series of synthetic analogues has been described, which have been evaluated mainly in in vitro systems . The synthetic tert ‐butylated analogs of resveratrol and the oligomers pallidol and quadrangularin A synthetized via biomimetic oxidative dimerization were recently reported to be more potent than their native counterparts at inhibiting the growth of TF1 leukemia cells .…”

“…The discovery that some resveratrol oligomers possess biological properties, including antifungal, antioxidant, antibacterial, antiviral, anti‐inflammatory, and antitumor properties (with some resveratrol oligomers reported to be superior to resveratrol), has continued to generate scientific interest in these derivatives. With the broad range of biological activities of resveratrol oligomers and their pharmacological potential for drug development, several research groups have successfully generated synthetic versions of these compounds with variable molecular complexity, mainly using biomimetic synthesis or de novo synthetic approaches …”

Resveratrol Functionalized Carboxymethyl-β-Cyclodextrin: Synthesis, Characterization, and Photostability

“…Resveratrol, 3,4′,5-trihydroxystilbene (Figure 1), is a type of naturally existing phenol and is widely used as food additive [1]. Resveratrol was found in many plants such as grapes, olives, blackberries, pines, and peanuts [2][3][4][5][6].…”

Application of Traditional Chinese Medicines in Postoperative Abdominal Adhesion

“…Resveratrol, one of the most important naturally active polyphenols, has some proven effects, such as antioxidant, anti-inflammatory, and antitumour [26,27]. Resveratrol not only reduces oxidative stress and inflammatory response but also modulates immune responses [28,29].…”