Stereoselective synthesis of (−)‐cytoxazone and its unnatural congener (+)‐5‐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...
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| Published in | Chirality (New York, N.Y.) Vol. 33; no. 8; pp. 479 - 489 |
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| 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. |
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| AbstractList | 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. 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 ((4 R ,5 R )‐ and (4 R ,5 S )‐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. 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. |
| Author | Purgato, Gislaine Aparecida Diaz‐Muñoz, Gaspar Santos, Pedro Henrique Costa Kohlhoff, Markus Miranda, Izabel Luzia Diaz, Marisa Alves Nogueira |
| Author_xml | – sequence: 1 givenname: Izabel Luzia surname: Miranda fullname: Miranda, Izabel Luzia organization: Federal University of Minas Gerais – sequence: 2 givenname: Pedro Henrique Costa surname: Santos fullname: Santos, Pedro Henrique Costa organization: Federal University of Minas Gerais – sequence: 3 givenname: Markus surname: Kohlhoff fullname: Kohlhoff, Markus organization: Oswaldo Cruz Foundation (Fiocruz) – sequence: 4 givenname: Gislaine Aparecida surname: Purgato fullname: Purgato, Gislaine Aparecida email: gislaine.aparecida@ufv.br organization: Federal University of Viçosa – sequence: 5 givenname: Marisa Alves Nogueira orcidid: 0000-0002-3370-4149 surname: Diaz fullname: Diaz, Marisa Alves Nogueira organization: Federal University of Viçosa – sequence: 6 givenname: Gaspar orcidid: 0000-0002-7515-0420 surname: Diaz‐Muñoz fullname: Diaz‐Muñoz, Gaspar email: gaspardm@qui.ufmg.br organization: Federal University of Minas Gerais |
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| Keywords | oxazolidinone d-4-hydroxyphenylglycine ENANTIOSELECTIVE SYNTHESIS ANALOGS CYTOKINE MODULATOR stereoisomer stereoselective addition CYTOXAZONE CONCISE SYNTHESIS (+)-EPI-CYTOXAZONE |
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| Snippet | An interesting protocol for stereoselective synthesis of (−)‐cytoxazone and its unnatural stereoisomer (+)‐5‐epi‐cytoxazone from d‐4‐hydroxyphenylglycine in... An interesting protocol for stereoselective synthesis of (-)-cytoxazone and its unnatural stereoisomer (+)-5-epi-cytoxazone from d-4-hydroxyphenylglycine in... An interesting protocol for stereoselective synthesis of (−)‐cytoxazone and its unnatural stereoisomer (+)‐5‐ epi ‐cytoxazone from d ‐4‐hydroxyphenylglycine in... |
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| SubjectTerms | 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 |
| Title | Stereoselective synthesis of (−)‐cytoxazone and its unnatural congener (+)‐5‐epi‐cytoxazone |
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