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Studies aiming the asymmetric total synthesis of caramboxin

Abstract

In 2013, brazilian researchers isolated the compound responsible for possible neurotoxic effects caused by the ingestion of star fruit (Averrhoa carambola) - the caramboxin. The structure contains a phenylalanine skeleton and the absolute configuration of carbon alfa-amino acid has only been inferred by comparison with the alfaD values of L-phenylalanine.To confirm the absolute configuration, this project proposes two studies to asymmetric total synthesis of caramboxine. In both studies, we will consider the 3,5-dihydroxybenzoic acid as starting material. The best route is evaluated in terms of performance and cost: or by diastereoselective alkylation of a glycine derivative (SCHOLLKOPF method) or through the Erlenmeyer-Plöchl reaction followed by enzymatic resolution of the amino acid. (AU)

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Scientific publications (4)
(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)
OLIVEIRA FILHO, RONALDO E.; HIGA, VANESSA M.; OMORI, ALVARO T.. Studies Toward the Synthesis of Caramboxin Analogues. Journal of the Brazilian Chemical Society, v. 30, n. 3, SI, p. 528-540, . (14/25659-8)
CAPELETTO, MARINA GONCALVES; DE OLIVEIRA FILHO, RONALDO EPIFANIO; DIONISIO, VICTOR YOKOO; OMORI, ALVARO TAKEO. Diazotization of Anilines in Vinegar: A Very Simple and Low-cost Synthesis of Iodoarenes and Arylfurans. CURRENT GREEN CHEMISTRY, v. 4, n. 2, p. 108-112, . (14/25659-8)
DA COSTA, MONIQUE RODRIGUES; OMORI, ALVARO TAKEO. Tween (R) 20-Enhanced Bioreduction of Acetophenones Promoted by Daucus carota Root. Food Technology and Biotechnology, v. 55, n. 2, p. 231-235, . (14/25659-8)
OMORI, ALVARO TAKEO; LOBO, FLAVIA GONCALVES; GONCALVES DO AMARAL, ANNA CAROLINA; DE OLIVEIRA, CAMILA DE SOUZA. Purple carrots: Better biocatalysts for the enantioselective reduction of acetophenones than common orange carrots (D. carota). JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, v. 127, p. 93-97, . (14/25659-8, 09/00617-2)

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