| dc.creator | Miranda, Izabel Luzia | |
| dc.creator | Santos, Pedro Henrique Costados | |
| dc.creator | Kohlhoff, Markus | |
| dc.creator | Purgato, Gislaine Aparecida | |
| dc.creator | Diaz, Marisa Alves Nogueira | |
| dc.creator | Muñoz, Gaspar Diaz | |
| dc.date | 2022-03-24T18:32:02Z | |
| dc.date | 2022-03-24T18:32:02Z | |
| dc.date | 2021 | |
| dc.date.accessioned | 2023-09-26T20:08:15Z | |
| dc.date.available | 2023-09-26T20:08:15Z | |
| dc.identifier | MIRANDA, Izabel Luzia et al. Stereoselective synthesis of (−)‐cytoxazone and its unnatural congener (+)‐5‐epi‐cytoxazone. Chirality, v. 33, n. 8, p. 479-489, 2021. doi.org/10.1002/chir.23334 | |
| dc.identifier | 0899-0042 | |
| dc.identifier | https://www.arca.fiocruz.br/handle/icict/51866 | |
| dc.identifier | 10.1002/chir.23334 | |
| dc.identifier.uri | https://repositorioslatinoamericanos.uchile.cl/handle/2250/8849424 | |
| dc.description | 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. | |
| dc.format | application/pdf | |
| dc.language | eng | |
| dc.publisher | Wiley Periodicals | |
| dc.rights | restricted access | |
| dc.subject | d‐4‐hydroxyphenylglycine | |
| dc.subject | oxazolidinone | |
| dc.subject | stereoisomer | |
| dc.subject | stereoselective addition | |
| dc.title | Stereoselective synthesis of (−)‐cytoxazone and its unnatural congener (+)‐5‐epi‐cytoxazone | |
| dc.type | Article | |
