Interest of organic chemistry in biomimetic synthesis is constantly increasing in order to obtain bioactive natural products in steps and atoms economy. In the light of these, during iodination of resveratrol as starting material to obtain natural compounds, unexpectedly, an interesting by-product was obtained. In fact, in addition to iodinated resveratrol NMR signals showed the presence of a compound with a 2,3-dihydrobenzofuran motif. The only explanation for this event is the radical generation on resveratrol by NIS, used as iodinating agent. Oxidation of the phenol moiety can generate a hypothetical phenoxyl radical, that leads to dimerization, affording to a 2,3- dihydrobenzofuran moiety. Therefore, formation of radical and subsequently dimerization, as naturally occurs, makes this strategy as a new biomimetic synthesis of resveratrol dimer. Herein, we present our study performed to optimize the 2,3-dihydrobenzofuran formation conditions and to identify the structure of the obtained compound. Methylation and dehalogenation reactions confirmed the formation of the permethylated (±)-e viniferin
Radical resveratrol dimerization to dihydrobenzofuran system by NIS
Rosarita D’Orsi
Primo
;
2020-01-01
Abstract
Interest of organic chemistry in biomimetic synthesis is constantly increasing in order to obtain bioactive natural products in steps and atoms economy. In the light of these, during iodination of resveratrol as starting material to obtain natural compounds, unexpectedly, an interesting by-product was obtained. In fact, in addition to iodinated resveratrol NMR signals showed the presence of a compound with a 2,3-dihydrobenzofuran motif. The only explanation for this event is the radical generation on resveratrol by NIS, used as iodinating agent. Oxidation of the phenol moiety can generate a hypothetical phenoxyl radical, that leads to dimerization, affording to a 2,3- dihydrobenzofuran moiety. Therefore, formation of radical and subsequently dimerization, as naturally occurs, makes this strategy as a new biomimetic synthesis of resveratrol dimer. Herein, we present our study performed to optimize the 2,3-dihydrobenzofuran formation conditions and to identify the structure of the obtained compound. Methylation and dehalogenation reactions confirmed the formation of the permethylated (±)-e viniferinI documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
