New Approach for the Stereoselective Synthesis of (+)-epi-Cytoxazone

• Published in: Journal of the Brazilian Chemical Society Vol. 30; no. 3; pp. 585 - 591
• Main Authors: Miranda, Izabel L., Sartori, Suelen K., Diaz, Marisa A. N., Diaz-Munoz, Gaspar
• Format: Journal Article
• Language: English
• Published: SAO PAULO Soc Brasileira Quimica 01.03.2019; Sociedade Brasileira de Química
• Subjects: Chemistry; CHEMISTRY, MULTIDISCIPLINARY; Physical Sciences; Science & Technology; stereoselective dihydroxylation; epi-cytoxazone; Wittig olefination; cytoxazone; RING; 2,3-O-(3-pentylidene)-(R)-glyceraldehyde; CYTOKINE MODULATOR; VERSATILE SYNTHESIS; OXAZOLIDINONES; (-)-CYTOXAZONE

The stereoselective total synthesis of (+)-epi-cytoxazone was performed satisfactorily in 8 steps, in 17% overall yield, via a novel route from 2,3-O-(3-pentylidene)-(R)-glyceraldehyde. The bulky group alkene-ketal allowed intramolecular control of the target molecule's asymmetric centers in th...