| Author | Miranda, Izabel Luzia | |
| Author | Santos, Pedro Henrique Costa Dos | |
| Author | Kohlhoff, Markus | |
| Author | Purgato, Gislaine Aparecida | |
| Author | Diaz, Marisa Alves Nogueira | |
| Author | Diaz-Muñoz, Gaspar | |
| Access date | 2022-12-14T18:53:18Z | |
| Available date | 2022-12-14T18:53:18Z | |
| Document date | 2021 | |
| Citation | MIRANDA, Izabel Luzia et al. Stereoselective synthesis of ()-cytoxazone and its unnatural congener (+)-5- epi -cytoxazone. CHIRALITY , v. 33, p. 479-489, 2021. doi.org/10.1002/chir.23334 | en_US |
| ISSN | 1520-636X | en_US |
| URI | https://www.arca.fiocruz.br/handle/icict/55943 | |
| Language | eng | en_US |
| Publisher | Wiley Periodicals | en_US |
| Rights | restricted access | |
| Title | Stereoselective synthesis of (-)-cytoxazone and its unnatural congener (+)-5-epi-cytoxazone | en_US |
| Type | Article | |
| Abstract | An interesting protocol for stereoselective synthesis of (−)-cytoxazone and its unnatural stereoisomer (+)-5-epi-cytoxazone from D-4-hydroxyphenylglycine in overall yields of 10% and 16%, respectively, is described. The stereoselective addition of cyanide to an N-Boc protected aminoaldehyde (tert-butyl ((R)-1-(4-methoxyphenyl)-2-oxoethyl)carbamate) (5) constitutes the key step in this approach, producing a mixture of cyanohydrins 6a and b (1,2-anti and 1,2-syn tert-butyl (2-cyano-2-hydroxy-1-(4-methoxyphenyl)ethyl)carbamate) in 89% yield, with reasonable stereoselectivity (1.0:1.8) in favor of the anti-Felkin product (1,2-syn). A one-pot sequence of three successive steps from this mixture produced the oxazolidinone isomers 9a and b ((4R,5R)- and (4R,5S)-4-(4-methoxyphenyl)-2-oxooxazolidine-5-carboxylate). Chromatographic column separation and reduction of the ester function of both precursors led to (−)-cytoxazone and (+)-5-epi-cytoxazone. | en_US |
| Affilliation | Department of Chemistry. Federal University of Minas Gerais. Belo Horizonte, MG, Brazil | en_US |
| Affilliation | Department of Chemistry. Federal University of Minas Gerais. Belo Horizonte, MG, Brazil | en_US |
| Affilliation | Chemistry of Bioactive Natural Products. René Rachou Institute. Oswaldo Cruz Foundation. Belo Horizonte, MG, Brazil | en_US |
| Affilliation | Department of Biochemistry and Molecular Biology. Federal University of Viçosa., Viçosa, MG, Brazil | en_US |
| Affilliation | Department of Biochemistry and Molecular Biology. Federal University of Viçosa., Viçosa, MG, Brazil | en_US |
| Affilliation | Department of Chemistry. Federal University of Minas Gerais. Belo Horizonte, MG, Brazil | en_US |
| Embargo date | 2096 | |
