Asymmetric synthesis of N,O,O,O-tetra-acetyl d-lyxo-phytosphingosine, jaspine B (pachastrissamine) and its C(2)-epimer

Tetrahedron Asymmetry

Volumn 18, Issue 21, 2007, Pages 2510-2513

  Abraham, Elin ^a   Candela Lena, José I ^a   Davies, Stephen G ^a   Georgiou, Matthew ^a   Nicholson, Rebecca L ^a   Roberts, Paul M ^a   Russell, Angela J ^a   Sánchez Fernández, Elena M ^a   Smith, Andrew D ^a   Thomson, James E ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMINE; CAMPHORSULFONYLOXAZIRIDINE; JASPINE B; LITHIUM; N BENZYL N ALPHA METHYLBENZYLAMIDE; OXAZIRIDINE DERIVATIVE; PHYTOSPHINGOSINE; SPHINGOSINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; EPIMER; OXIDATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 36148970785     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.10.026     Document Type: Article

References (50)

1. Bergmeier S.C. Tetrahedron 56 (2000) 2561
2. Cinque B., Di Marzio L., Centi C., Di Rocco C., Riccardi C., and Cifone M.G. Pharmacol. Res. 47 (2003) 421
3. For a review see:. Howell A.R., and Ndakala A.J. Curr. Org. Chem. 6 (2002) 365
4. Kuroda I., Musman M., Ohtani I.I., Ichiba T., Tanaka J., Garcia-Gravalos D., and Higa T. J. Nat. Prod. 65 (2002) 1505
5. Ledroit V., Debitus C., Lavaud C., and Massoit G. Tetrahedron Lett. 44 (2003) 225
6. Sudhakar N., Ravi Kumar A., Prabhakar A., Jagadeesh B., and Rao B.V. Tetrahedron Lett. 46 (2005) 325
7. Bhaket P., Morris K., Stauffer C.S., and Datta A. Org. Lett. 7 (2005) 875
8. Du Y., Liu J., and Linhardt R.J. J. Org. Chem. 71 (2006) 1251
9. Liu J., Du Y., Dong X., Meng S., Xiao J., and Cheng L. Carbohydr. Res. 341 (2006) 2653
10. Ribes C., Falomir E., Carda M., and Marco J.A. Tetrahedron 62 (2006) 5421
11. van den. Berg R.J.B.H.N., Boltje T.J., Verhagen C.P., Litjens R.E.J.N., van der Marel G.A., and Overkleeft H.S. J. Org. Chem. 71 (2006) 836
12. Lee T., Lee S., Kwak Y.S., Kim D., and Kim S. Org. Lett. 9 (2007) 429
13. Ramana C.V., Giri A.G., Suryawanshi S.B., and Gonnade R.G. Tetrahedron Lett. 48 (2007) 265
14. Reddy L.V.R., Reddy P.V., and Shaw A.K. Tetrahedron: Asymmetry 18 (2007) 542
15. Prasad K.R., and Chandrakumar A. J. Org. Chem. 72 (2007) 6312
16. Yakura T., Sato S., and Yoshimoto Y. Chem. Pharm. Bull. 55 (2007) 1284
17. Chandrasekhar S., Tiwari B., and Prakash S.J. ARKIVOC (2006) 155
18. Génisson Y., Lamandé L., Salma Y., Andrieu-Abadie N., André C., and Baltas M. Tetrahedron: Asymmetry 18 (2007) 857
19. For a review concerning the application of the conjugate addition of homochiral lithium amides see:. Davies S.G., Smith A.D., and Price P.D. Tetrahedron: Asymmetry 16 (2005) 2833
20. Bunnage M.E., Chernega A.N., Davies S.G., and Goodwin C.J. J. Chem. Soc., Perkin Trans. 1 (1994) 2373
21. Bunnage M.E., Davies S.G., and Goodwin C.J. Synlett (1993) 731
22. Bunnage M.E., Davies S.G., and Goodwin C.J. J. Chem. Soc., Perkin Trans. 1 (1993) 1375
23. Bunnage M.E., Burke A.J., Davies S.G., and Goodwin C.J. Tetrahedron: Asymmetry 5 (1994) 203
24. Bunnage M.E., Davies S.G., and Goodwin C.J. J. Chem. Soc., Perkin Trans. 1 (1994) 2385
25. Bunnage M.E., Burke A.J., Davies S.G., and Goodwin C.J. Tetrahedron: Asymmetry 6 (1995) 165
26. Burke A.J., Davies S.G., and Hedgecock C.J.R. Synlett (1996) 621
27. Bunnage M.E., Burke A.J., Davies S.G., Millican N.L., Nicholson R.L., Roberts P.M., and Smith A.D. Org. Biomol. Chem. 1 (2003) 3708
28. Davies S.G., Hughes D.G., Nicholson R.L., Smith A.D., and Wright A.J. Org. Biomol. Chem. 2 (2004) 1549
29. Hayes M.P., Hatala P.J., Sherer B.A., Tong X., Zanatta N., Borer P.N., and Kallmerten J. Tetrahedron 57 (2001) 1515
30. Enders D., and Schusseler T. Synthesis (2002) 2280
31. 1H NMR spectrum of the crude reaction product.
32. Costello J.F., Davies S.G., and Ichihara O. Tetrahedron: Asymmetry 5 (1994) 3919
33. Campbell A.D., Raynham T.M., and Taylor R.J.K. Synthesis (1998) 1707
34. Unreacted starting material 6 was recovered and recycled.
35. Frigerio M., and Santagostino M. Tetrahedron Lett. 35 (1994) 8019
36. Frigerio M., Santagostino M., Sputore S., and Palmesano G. J. Org. Chem. 60 (1995) 7272
37. IBX was prepared from 2-iodobenzoic acid according to the procedure of. Frigerio M., Santagostino M., and Sputore S. J. Org. Chem. 64 (1999) 4537
38. Tetradecylmagnesium bromide was prepared as a solution in THF from 1-bromotetradecane and magnesium turnings.
39. 1H NMR spectrum of the crude reaction product. However, hydrolysis of the crude reaction mixture followed by peracetylation gave a 90:10 mixture of the corresponding N,O,O,O-tetra-acetyl phytosphingosines 12 and 13.
40. The configurations of 10 and 11 could not be assigned a priori; they were determined by correlation to the corresponding N,O,O,O-tetra-acetyl phytosphingosines 12 and 13. The (4S,5S,1′S)-configuration of the major diastereoisomeric product 10 is consistent with Si face attack of the Grignard on aldehyde 9 via a chelated Cram model; see:. Cram D.J., and Elhafez F.A.A. J. Am. Chem. Soc. 74 (1952) 5828
41. Cram D.J., and Kopecky K.R. J. Am. Chem. Soc. 81 (1959) 2748
42. Shirota O., Nakanishi K., and Berova N. Tetrahedron 55 (1999) 13643
43. Jo S.Y., Kim H.C., Jeon D.J., and Kim H.R. Heterocycles 55 (2001) 1127
44. +) requires 300.2897; found, 300.2900.
45. 36 Crystallographic data (excluding structure factors) have been deposited with the Cambridge Crystallographic Data Centre as Supplementary Publication Number CCDC 616170. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk].
46. Betteridge, P. W.; Carruthers, J. R.; Cooper, R. I.; Prout, C. K.; Watkin, D. J. crystals, Department of Chemical Crystallography, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK, 2001.
47. Flack H.D., and Bernardelli G. Acta. Crystallogr., Sect. A 55 (1999) 908
48. Dale J.A., and Mosher H.S. J. Am. Chem. Soc. 95 (1973) 512
49. Sullivan G.R., Dale J.A., and Mosher H.S. J. Org. Chem. 38 (1973) 2143
50. Ohtani I., Kusumi T., Kashman Y., and Kakisawa H. J Am. Chem. Soc. 113 (1991) 4092