Stereoselective synthesis of (−)‐cytoxazone and its unnatural congener (+)‐5‐epi‐cytoxazone

• Published in: Chirality (New York, N.Y.) Vol. 33; no. 8; pp. 479 - 489
• Main Authors: Miranda, Izabel Luzia, Santos, Pedro Henrique Costa, Kohlhoff, Markus, Purgato, Gislaine Aparecida, Diaz, Marisa Alves Nogueira, Diaz‐Muñoz, Gaspar
• Format: Journal Article
• Language: English
• Published: HOBOKEN Wiley 01.08.2021; Wiley Subscription Services, Inc
• Subjects: Chemistry; Chemistry, Analytical; Chemistry, Medicinal; Chemistry, Organic; Congeners; Cyanides; d‐4‐hydroxyphenylglycine; Isomers; Life Sciences & Biomedicine; oxazolidinone; Pharmacology & Pharmacy; Physical Sciences; Science & Technology; stereoisomer; Stereoisomerism; Stereoisomers; stereoselective addition; Stereoselectivity; Synthesis; oxazolidinone; d-4-hydroxyphenylglycine; ENANTIOSELECTIVE SYNTHESIS; ANALOGS; CYTOKINE MODULATOR; stereoisomer; stereoselective addition; CYTOXAZONE; CONCISE SYNTHESIS; (+)-EPI-CYTOXAZONE

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‐bu...