Asymmetric α-chloroallylboration of amino aldehydes: A novel and highly versatile route to D- and L-erythro-sphingoid bases

Journal of Organic Chemistry

Volumn 64, Issue 12, 1999, Pages 4426-4430

  Hertweck, Christian ^a   Boland, Wilhelm ^a  

^a MAX PLANCK INSTITUTE FOR CHEMICAL ECOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 EPOXY 3 BUTENE; ALDEHYDE; AMINOALCOHOL; BORANE DERIVATIVE; OXAZOLIDINE DERIVATIVE; SPHINGOSINE DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; DIASTEREOISOMER; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

EID: 0033546109     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990117+     Document Type: Article

References (58)

1. (a) Hannun, Y. A.; Bell, R. M. Science 1989, 243, 500.
2. (b) Merrill, A. H.; Nimkar, S.; Menaldino, D.; Hannun, Y. A.; Loomis, C.; Bell, R. M.; Tyagi, S. R.; Lambeth, J. D.; Stevens, V. L.; Hunter, R.; Liotta, D. C. Biochemistry 1989, 28, 3138.
3. (a) Kanfer, J. N.; Hakomori, S. Handbook of Lipid Research, Vol. 3 Sphingolipid Biochemistry; Hanahan, D. J., Ed.; Plenum Press: New York, 1983.
4. (b) Merrill, A. H., Jr.; Sweeley, C. C. In Biochemistry of Lipids, Lipoproteins and Membranes; Vance, D. E., Vance, J. E., Eds.; Elsevier Science B. V.: Amsterdam, 1996; p 309.
5. (a) Bell, R. M.; Hannun, Y. A. Merrill, A. H., Jr. (Eds.) Advances in Lipid Research: Sphingolipids and their Metabolites; Academic Press: Orlando, FL, 1993; Vols. 25 & 26.
6. (b) Hannun, Y. A. Sphingolipid-Mediated Signal Transduction; Chapman & Hall: New York, 1997.
7. (c) Pyne, S.; Tolan, D. G.; Conway, A. M.; Pyne, N. Biochem. Soc. Trans. 1997, 25, 549.
8. (d) Igarashi, Y. J. Biochem. 1997, 122, 1080.
9. (a) Ariga, T.; Jarvis, W. D.; Yu, R. K. J. Lipid Res. 1998, 39, 1.
10. (b) Sweeney, E. A.; Sakakura, C.; Shirahama, T.; Masamune, A.; Ohta, H.; Hakomori, S.; Igarashi, Y. Int. J. Cancer 1996, 66, 358.
11. Zhang, H.; Desai, N. N.; Olivera, A.; Seki, T.; Brooker, G.; Spiegel, S. J. Cell Biol. 1991, 114, 155.
12. Karlsson, K.-A. Lipids 1970, 5, 878.
13. For an example of an antiviral sphingosine derivative, isolated from green alga Ulva fasciata, see: Garg, H. S.; Sharma, M.; Bhakuni, D. S.; Pramanik B. N.; Bose, A. K. Tetrahedron Lett. 1992, 33, 1641.
14. For an example of antitumor cerebrosides (agelaphins) from marine sponge Agelas mauritianus, see: Naroti, T.; Morita, M.; Akimoto, K.; Koezuka Y. Tetrahedron 1994, 50, 2771.
15. For antibiotic properties of aplidiasphingosine (4), isolated from Aplidium sp. (tunicate), see: Carter, G. T.; Rinehart, K. L. J. Am. Chem. Soc. 1978, 100, 7441.
16. Sachs, C. W.; Ballas, L. M.; Mascarella, S. W.; Safa, A. R.; Lewin, A. H.; Loomis, C.; Carroll, F. I.; Bell, R. M.; Fine, R. L. Biochem. Pharmacol. 1996, 52, 603.
17. For a comprehensive review on sphingosine syntheses, see: (a) Koskinen, P. M.; Koskinen, A. M. P. Synthesis 1998, 1075, and references cited herein. (b) Hoffman, R. V.; Tao, J. J. Org. Chem. 1998, 63, 3979-3985. Nugent, T. C.; Hudlicky, T. J. Org. Chem. 1998, 63, 510.
18. For a comprehensive review on sphingosine syntheses, see: (a) Koskinen, P. M.; Koskinen, A. M. P. Synthesis 1998, 1075, and references cited herein. (b) Hoffman, R. V.; Tao, J. J. Org. Chem. 1998, 63, 3979-3985. Nugent, T. C.; Hudlicky, T. J. Org. Chem. 1998, 63, 510.
19. For a comprehensive review on sphingosine syntheses, see: (a) Koskinen, P. M.; Koskinen, A. M. P. Synthesis 1998, 1075, and references cited herein. (b) Hoffman, R. V.; Tao, J. J. Org. Chem. 1998, 63, 3979-3985. Nugent, T. C.; Hudlicky, T. J. Org. Chem. 1998, 63, 510.
20. Hertweck, C.; Boland, W. Recent Approaches Using Alkenyl-oxiranes in Organic Chemistry. In Recent Research Developments in Organic Chemistry; Pandalai, S. G., Ed.; Transworld Research Network: 1999, in print.
21. (a) Murakami, T.; Hato, M. J. Chem. Soc., Perkin Trans. 1 1996, 8, 823.
22. (b) Murakami, T.; Shimizu, T. Synth. Commun. 1997, 27, 4255.
23. Nakagawa, M.; Tsuruoka, A.; Yoshida, J.; Hino, T. J. Chem. Soc., Chem. Commun. 1990, 8, 603.
24. Hertweck, C.; Goerls, H.; Boland, W. J. Chem. Soc., Chem. Commun. 1998, 18, 1955-1956.
25. Marshall, J. A. Chem. Rev. 1989, 89, 1503, and references cited herein.
26. (a) Jayaraman, S.; Hu, S.; Oehlschlager, A. C. Tetrahedron Lett. 1995, 36, 4765.
27. (b) Hu, S.; Jayaraman, S.; Oehlschlager, A. C. J. Org. Chem. 1996, 61, 7513.
28. Brown, H. C.; Ramachandran, P. V. J. Organomet. Chem. 1995, 500, 1.
29. Hertweck, C.; Boland, W. J. Prakt. Chem. 1999, 341, 83.
30. Garner, P.; Park, J. M. J. Org. Chem. 1987, 52, 2361.
31. (a) Garner, P.; Park, J. M. Org. Synth. 1992, 70, 18.
32. (b) McKillop, A.; Taylor, R. J. K.; Watson, R. J.; Lewis, N. Synthesis 1994, 31.
33. (c) Dondoni, A.; Perrone, D. Synthesis 1997, 527.
34. (d) Meffre, P.; Durand, P.; Branquet, E.; Le Goffic, F. Synth. Commun. 1994, 24, 2147.
35. For mild oxidation of serinol using the Dess-Martin-reagent see: Avenoza, A.; Cativiela, C.; Corzana, F.; Peregrina, J. M.; Zurbano, M. M. Synthesis 1997, 1146.
36. Barrett, A. G. M.; Edmunds, J. J.; Hendrix, J. A.; Malecha, J. W.; Parkinson, C. J. J. Chem. Soc., Chem. Commun. 1992, 1240.
37. Brown, H. C.; Racherla, U. S.; Liao, Y.; Khanna, V. V. J. Org. Chem. 1992, 57, 6608.
38. Hu, S.; Jayaraman, S.; Oehlschlager, A. C. J. Org. Chem. 1998, 63, 8843.
39. For other examples of substrate control in pinene based allylborations, see: (a) Burgess, K.; Henderson, I. Tetrahedron Lett. 1990, 31, 6949. (b) Barrett, A. G. M.; Malecha, J. W. J. Org. Chem. 1991, 56, 5243. Barrett, A. G. M.; Seefeld, M. A.; White, A. J. P. Williams, D. J. J. Org. Chem. 1996, 61, 2677.
40. For other examples of substrate control in pinene based allylborations, see: (a) Burgess, K.; Henderson, I. Tetrahedron Lett. 1990, 31, 6949. (b) Barrett, A. G. M.; Malecha, J. W. J. Org. Chem. 1991, 56, 5243. Barrett, A. G. M.; Seefeld, M. A.; White, A. J. P. Williams, D. J. J. Org. Chem. 1996, 61, 2677.
41. For other examples of substrate control in pinene based allylborations, see: (a) Burgess, K.; Henderson, I. Tetrahedron Lett. 1990, 31, 6949. (b) Barrett, A. G. M.; Malecha, J. W. J. Org. Chem. 1991, 56, 5243. Barrett, A. G. M.; Seefeld, M. A.; White, A. J. P. Williams, D. J. J. Org. Chem. 1996, 61, 2677.
42. Hertweck, C.; Boland, W. Tetrahedron 1997, 53, 14651.
43. Hertweck, C.; Boland, W. Eur. J. Org. Chem. 1998, 2143, 3.
44. Schwesinger, R. Nachr. Chem. Technol. Lab. 1990, 38, 1214.
45. Marshall, J. A.; Crute, T. D., III; Hai, J. D. J. Org. Chem. 1992, 57, 115.
46. Bailey, W. F.; Ovaska, T. V.; Leipert, T. K. Tetrahedron Lett. 1989, 30, 3901.
47. For the influence of steric factors on cuprate additions see: (a) Marshall, J. A.; Trometer, J. D.; Blough, B. E.; Crute, T. D. J. J. Org. Chem. 1988, 53, 4274. For the influence of solvents see: (b) Schlecht, M. F. J. J. Chem. Soc., Chem. Commun. 1982, 1331. For electronic factors affecting (E)-stereospecificity and theoretical background of cuprate addition, see: (c) Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1984, 25, 3063. Hamon, L.; Levisalles, J. Tetrahedron 1989, 45, 489.
48. For the influence of steric factors on cuprate additions see: (a) Marshall, J. A.; Trometer, J. D.; Blough, B. E.; Crute, T. D. J. J. Org. Chem. 1988, 53, 4274. For the influence of solvents see: (b) Schlecht, M. F. J. J. Chem. Soc., Chem. Commun. 1982, 1331. For electronic factors affecting (E)-stereospecificity and theoretical background of cuprate addition, see: (c) Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1984, 25, 3063. Hamon, L.; Levisalles, J. Tetrahedron 1989, 45, 489.
49. For the influence of steric factors on cuprate additions see: (a) Marshall, J. A.; Trometer, J. D.; Blough, B. E.; Crute, T. D. J. J. Org. Chem. 1988, 53, 4274. For the influence of solvents see: (b) Schlecht, M. F. J. J. Chem. Soc., Chem. Commun. 1982, 1331. For electronic factors affecting (E)-stereospecificity and theoretical background of cuprate addition, see: (c) Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1984, 25, 3063. Hamon, L.; Levisalles, J. Tetrahedron 1989, 45, 489.
50. For the influence of steric factors on cuprate additions see: (a) Marshall, J. A.; Trometer, J. D.; Blough, B. E.; Crute, T. D. J. J. Org. Chem. 1988, 53, 4274. For the influence of solvents see: (b) Schlecht, M. F. J. J. Chem. Soc., Chem. Commun. 1982, 1331. For electronic factors affecting (E)-stereospecificity and theoretical background of cuprate addition, see: (c) Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1984, 25, 3063. Hamon, L.; Levisalles, J. Tetrahedron 1989, 45, 489.
51. Radunz, H.-E.; Devant, R. M.; Eiermann, V. Liebigs Ann. Chem. 1988, 1103.
52. Dondoni, A.; Fantin, G.; Fogagnolo, M.; Pedrini, P. J. Org. Chem. 1990, 55, 1439.
53. Garner, P.; Park, J. M.; Malecki, E. J. Org. Chem. 1988, 53, 4395.
54. Murakami, M.; Iwama, S.; Fujii, S.; Ikeda, K.; Kataumara, S.; Bioorg. Med. Chem. Lett. 1997, 7, 1725,
55. Use of a ω-functionalized sphingoid base for affinity chromatography has been reported: Kozikowski, A. P.; Ding, Q.; Spiegel, S. Tetrahedron Lett. 1996, 37, 3279.
56. Knochel, P.; Perea, J. J. A.; Jones, P. Tetrahedron 1998, 54, 8275.
57. Trost, B. M.; Scanlan, T. S. J. Am. Chem. Soc. 1989, 111, 4988.
58. Suzuki, K.; Hasegawa, T.; Imai, T.; Maeta, H.; Ohba, S. Tetrahedron 1995, 51, 4483.