Phenylpropenes or allylbenzenes derivatives are the skeletons of many biologically important natural products as gingerol, eugenol, chavicol, safrole and estragole (1). They are also precursors of Lignans and Stegane structures which are studied for their important activities (2). In this work we report a rapid and efficient methodology to obtain various phenylpropenes 1 performing a [3,3]-sigmatropic Claisen rearrangement of compounds 2 (3). The protected phenols could be easily prepared from substrates 3 with an allylation reaction on the corresponding free hydroxyl group. (Figure 2). With this synthetical approach we are able to synthesize the 1,2,3,4-tetramethoxy-5-(2-propenil)benzene, an antibacterical natural product (4), in only 4 steps and 58% overall yield. (1) Koeduka, T. Plant Biotechnol. 2014, 31, 401–407. (2) Chang, J.; Reiner, J.; Xie, J. Chem. Rev. 2005, 105, 4581–4609. (3) Tripathi, S.; Chan, M.-H.; Chen, C. Bioorg. Med. Chem. Lett. 2012, 22, 216–221. (4) Trikojus, V. M.; White, D. E. J. Chem. Soc. Resumed 1949, 436–439.
[3,3]-sigmatropic Claisen rearrangement: a rapid access to Phenylpropenes and Lignan structures / Bochicchio, Antonella; Chiummiento, Lucia; Cefola, Rossella; Funicello, Maria; Lupattelli, Paolo. - (2015), pp. 10-10. (Intervento presentato al convegno XVI Convegno Reazioni Pericicliche e Sintesi di Etero e Carbocicli tenutosi a Matera).
[3,3]-sigmatropic Claisen rearrangement: a rapid access to Phenylpropenes and Lignan structures
LUPATTELLI, Paolo
2015
Abstract
Phenylpropenes or allylbenzenes derivatives are the skeletons of many biologically important natural products as gingerol, eugenol, chavicol, safrole and estragole (1). They are also precursors of Lignans and Stegane structures which are studied for their important activities (2). In this work we report a rapid and efficient methodology to obtain various phenylpropenes 1 performing a [3,3]-sigmatropic Claisen rearrangement of compounds 2 (3). The protected phenols could be easily prepared from substrates 3 with an allylation reaction on the corresponding free hydroxyl group. (Figure 2). With this synthetical approach we are able to synthesize the 1,2,3,4-tetramethoxy-5-(2-propenil)benzene, an antibacterical natural product (4), in only 4 steps and 58% overall yield. (1) Koeduka, T. Plant Biotechnol. 2014, 31, 401–407. (2) Chang, J.; Reiner, J.; Xie, J. Chem. Rev. 2005, 105, 4581–4609. (3) Tripathi, S.; Chan, M.-H.; Chen, C. Bioorg. Med. Chem. Lett. 2012, 22, 216–221. (4) Trikojus, V. M.; White, D. E. J. Chem. Soc. Resumed 1949, 436–439.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
