A rapid and highly diastereoselective synthesis of enantiomerically pure (4 R,5 R)- and (4 S,5 S)-isocytoxazone

Synlett

Volumn , Issue 10, 2011, Pages 1399-1402

  Buckley, Benjamin R ^a   Page, Philip C Bulman ^b   McKee, Vickie ^a  

^a LOUGHBOROUGH UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF EAST ANGLIA   (United Kingdom)

Author keywords

cytoxazone; diastereoselective; oxazolidinone; oxidation; tyrosine

Indexed keywords

ISOCYTOXAZONE; METHYL 5 [4 METHOXYPHENYL] 1,3 OXAZOLIDIN 2 ONE 4 CARBOXYLIC ACID; O METHYL N TERT BUTOXYCARBONYL TYROSINE METHYL ESTER; OXAZOLIDINONE DERIVATIVE; PEROXYDISULFATE POTASSIUM; TYROSINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; DIAZOTIZATION; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGENATION; METHYLATION; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 79958088800     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1260561     Document Type: Article

References (27)

1. Kakeya H, Morishita M, Kobinta K, Osono M, Ishizuka M, Osada H, J. Antibiot. 1998 51 1126
2. Carter P H., LaPorte J R., Scherle P A., Decicco [nl]C P., Bioorg. Med. Chem. Lett. 2003 13 1237
3. Kumar A R., Bhaskar G, Madhan A, Rao B V., Synth. Commun. 2003 33 2907
4. Narina S V., Kumar T S., George S, Sudalai A, Tetrahedron Lett. 2007 48 65
5. Hamersak Z, Sepac D, Ziher D, unjic V, Synthesis 2003 375
6. Giorgio E, Viglione R G., Zanasi R, Rosini C, J. Am. Chem. Soc. 2004 126 12968
7. Giorgio E, Roje M, Tanaka K, Hamersak Z, unjic V, Nakanishi K, Rosini C, Berova N, J. Org. Chem. 2005 70 6557
8. Kakeya H, Morishita M, Koshino H, Morita T, Kobayashi K, Osada H, J. Org. Chem. 1999 64 1052
9. Rozwadowska M D., Tomczak A, Tetrahedron: Asymmetry 2009 20 2048
10. Page P C. B., Rassias G A., Barros D, Adel A, Buckley B, Bethell D, Smith T A. D., Slawin A M. Z., J. Org. Chem. 2001 66 6926
11. Page P C. B., Barros D, Buckley B R., Marples B A., Tetrahedron: Asymmetry 2005 16 3488
12. Page P C. B., Rassias G R., Barros D, Ardakani A, Bethell D, Merifield E, Synlett 2002 580
13. Page P C. B., Buckley B R., Barros D, Blacker A J., Heaney H, Marples B A., Tetrahedron 2006 62 6607
14. Page P C. B., Buckley B R., Rassias G A., Blacker A J., Eur. J. Org. Chem. 2006 803
15. Page P C. B., Buckley B R., Heaney H, Blacker A J., Org. Lett. 2005 7 375
16. Page P C. B., Barros D, Buckley B R., Ardakani A, Marples B A., J. Org. Chem. 2004 69 3595
17. Page P C. B., Buckley B R., Blacker A J., Org. Lett. 2004 6 1543
18. Racioppi R, Gavagnin M, Strazzullo G, Sodano G, Tetrahedron Lett. 1990 31 5177
19. Macdiarmid J E., Qui L D., J. Org. Chem. 1981 46 1451
20. 5: 309.1576; found: 309.1578.
21. Shimamoto K, Ohfune Y, Tetrahedron Lett. 1988 29 5177
22. 3). IR (film): 3316, 2956, 2362, 2337, 1762, 1613, 1515, 1382, 1250, 1224, 1026, 834, 763 cm1. 1H NMR (400 MHz, CDCl3): δ = 3.81 (s, 3 H), 3.83 (s, 3 H), 4.31 (d, 1 H, J = 5.2 Hz), 5.56 (d, 1 H, J = 5.2 Hz), 6.81 (s, 1 H), 6.93 (d, 2 H, J = 4.8 Hz), 7.33 (d, 2 H, J = 4.8 Hz), 13C NMR (100 MHz, CDCl3): δ = 53.5, 55.7, 61.8, 79.9, 114.7, 127.5, 130.3, 158.6, 160.6, 170.7. HRMS: m/z [M+] calcd for C12H13NO5: 251.0794; found: 251.0794.
23. 3. 5035 data (1542 unique, Rint = 0.0157) collected on an Apex II diffractometer at 150 K. Solved by direct methods16 and refined by full-matrix least squares on F2. R1[I > 2s(I)] = 0.0298 and wR2 (all data) = 0.0745. Goodness of fit on F2 = 1.079. CCDC No. 804096.
24. 4), and the solvents were removed to afford an off-white solid, which was recrystallized from EtOAclight petroleum to give (4R,5R)-isocytoxazone (ent-3) as a colourless crystalline solid (1.75 g, 90%); mp 140142 °C; [a]20 D +74.8 (c 1.08, acetone), lit.3 [a]25 D +70 (c = 0.4, MeOH). IR (nujol): 3239, 1725, 1614, 1514, 1459, 1376, 1251, 1174, 1062, 1016, 828 cm1. 1H NMR (250 MHz, acetone-d6): δ = 3.713.87 (m, 3 H), 3.86 (s, 3 H), 5.35 (d, 1 H, J = 5.3 Hz), 7.01 (d, 2 H, J = 8.6 Hz), 7.41 (d, 2 H, J = 8.6 Hz). 13C NMR (100 MHz, CDCl3): δ = 56.0, 63.1, 64.2, 80.4, 115.4, 128.7, 133.2, 159.6, 161.3. HRMS: m/z [M+] calcd for C11H13NO4: 223.0845; found: 223.0842.
25. See the Supporting Information for the experimental data.
26. Ross A J., Lang H L., Jackson R F. W., J. Org. Chem. 2010 75 245
27. Sheldrick G M., Acta Crystallogr., Sect. A 2008 64 112