Stereoselective synthesis of D-erythro- and L-threo-sphinganines via palladium-catalyzed equilibration and Suzuki coupling

Tetrahedron Letters

Volumn 43, Issue 50, 2002, Pages 9027-9029

  Cook, Gregory R ^a   Pararajasingham, Ketheeswaran ^a  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DEXTRO ERYTHRO SPHINGANINE; LEVO THREO SPHINGANINE; OXAZOLINE DERIVATIVE; PALLADIUM; SPHINGANINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; EQUILIBRATION; HYDROBORATION; HYDROPHOBICITY; ISOMERISM; STEREOCHEMISTRY; SUZUKI REACTION; SYNTHESIS;

LATEOLABRAX JAPONICUS;

EID: 0037049166     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02309-2     Document Type: Article

References (26)

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9. For recent synthetic approaches to sphinganines, see: (a) Ndakala, A. J.; Hashemzadeh, M.; So, R. C.; Howell, A. R. Org. Lett. 2002, 4, 1719-1722; (b) Hertweck, C.; Sebek, P.; Svatos, A. Synlett 2001, 1965-1967; (c) He, L.; Byun, H.-S.; Bittman, R. J. Org. Chem. 2000, 65, 7618-7626; (d) Fernandes, R. A.; Kumar, P. Eur. J. Org. Chem. 2000, 3447-3449; (e) Azuma, H.; Tamagaki, S.; Ogino, K. J. Org. Chem. 2000, 65, 3538-3541; (f) Fernandes, R. A.; Kumar, P. Tetrahedron: Asymmetry 1999, 10, 4797-4802; (g) Villard, R.; Fotiadu, F.; Buono, G. Tetrahedron: Asymmetry 1998, 9, 607-611; (h) Hoffman, R. V.; Tao, J. J. Org. Chem. 1998, 63, 3979-3985.
10. For recent synthetic approaches to sphinganines, see: (a) Ndakala, A. J.; Hashemzadeh, M.; So, R. C.; Howell, A. R. Org. Lett. 2002, 4, 1719-1722; (b) Hertweck, C.; Sebek, P.; Svatos, A. Synlett 2001, 1965-1967; (c) He, L.; Byun, H.-S.; Bittman, R. J. Org. Chem. 2000, 65, 7618-7626; (d) Fernandes, R. A.; Kumar, P. Eur. J. Org. Chem. 2000, 3447-3449; (e) Azuma, H.; Tamagaki, S.; Ogino, K. J. Org. Chem. 2000, 65, 3538-3541; (f) Fernandes, R. A.; Kumar, P. Tetrahedron: Asymmetry 1999, 10, 4797-4802; (g) Villard, R.; Fotiadu, F.; Buono, G. Tetrahedron: Asymmetry 1998, 9, 607-611; (h) Hoffman, R. V.; Tao, J. J. Org. Chem. 1998, 63, 3979-3985.
11. For recent synthetic approaches to sphinganines, see: (a) Ndakala, A. J.; Hashemzadeh, M.; So, R. C.; Howell, A. R. Org. Lett. 2002, 4, 1719-1722; (b) Hertweck, C.; Sebek, P.; Svatos, A. Synlett 2001, 1965-1967; (c) He, L.; Byun, H.-S.; Bittman, R. J. Org. Chem. 2000, 65, 7618-7626; (d) Fernandes, R. A.; Kumar, P. Eur. J. Org. Chem. 2000, 3447-3449; (e) Azuma, H.; Tamagaki, S.; Ogino, K. J. Org. Chem. 2000, 65, 3538-3541; (f) Fernandes, R. A.; Kumar, P. Tetrahedron: Asymmetry 1999, 10, 4797-4802; (g) Villard, R.; Fotiadu, F.; Buono, G. Tetrahedron: Asymmetry 1998, 9, 607-611; (h) Hoffman, R. V.; Tao, J. J. Org. Chem. 1998, 63, 3979-3985.
12. For recent synthetic approaches to sphinganines, see: (a) Ndakala, A. J.; Hashemzadeh, M.; So, R. C.; Howell, A. R. Org. Lett. 2002, 4, 1719-1722; (b) Hertweck, C.; Sebek, P.; Svatos, A. Synlett 2001, 1965-1967; (c) He, L.; Byun, H.-S.; Bittman, R. J. Org. Chem. 2000, 65, 7618-7626; (d) Fernandes, R. A.; Kumar, P. Eur. J. Org. Chem. 2000, 3447-3449; (e) Azuma, H.; Tamagaki, S.; Ogino, K. J. Org. Chem. 2000, 65, 3538-3541; (f) Fernandes, R. A.; Kumar, P. Tetrahedron: Asymmetry 1999, 10, 4797-4802; (g) Villard, R.; Fotiadu, F.; Buono, G. Tetrahedron: Asymmetry 1998, 9, 607-611; (h) Hoffman, R. V.; Tao, J. J. Org. Chem. 1998, 63, 3979-3985.
13. For recent synthetic approaches to sphinganines, see: (a) Ndakala, A. J.; Hashemzadeh, M.; So, R. C.; Howell, A. R. Org. Lett. 2002, 4, 1719-1722; (b) Hertweck, C.; Sebek, P.; Svatos, A. Synlett 2001, 1965-1967; (c) He, L.; Byun, H.-S.; Bittman, R. J. Org. Chem. 2000, 65, 7618-7626; (d) Fernandes, R. A.; Kumar, P. Eur. J. Org. Chem. 2000, 3447-3449; (e) Azuma, H.; Tamagaki, S.; Ogino, K. J. Org. Chem. 2000, 65, 3538-3541; (f) Fernandes, R. A.; Kumar, P. Tetrahedron: Asymmetry 1999, 10, 4797-4802; (g) Villard, R.; Fotiadu, F.; Buono, G. Tetrahedron: Asymmetry 1998, 9, 607-611; (h) Hoffman, R. V.; Tao, J. J. Org. Chem. 1998, 63, 3979-3985.
14. For recent synthetic approaches to sphinganines, see: (a) Ndakala, A. J.; Hashemzadeh, M.; So, R. C.; Howell, A. R. Org. Lett. 2002, 4, 1719-1722; (b) Hertweck, C.; Sebek, P.; Svatos, A. Synlett 2001, 1965-1967; (c) He, L.; Byun, H.-S.; Bittman, R. J. Org. Chem. 2000, 65, 7618-7626; (d) Fernandes, R. A.; Kumar, P. Eur. J. Org. Chem. 2000, 3447-3449; (e) Azuma, H.; Tamagaki, S.; Ogino, K. J. Org. Chem. 2000, 65, 3538-3541; (f) Fernandes, R. A.; Kumar, P. Tetrahedron: Asymmetry 1999, 10, 4797-4802; (g) Villard, R.; Fotiadu, F.; Buono, G. Tetrahedron: Asymmetry 1998, 9, 607-611; (h) Hoffman, R. V.; Tao, J. J. Org. Chem. 1998, 63, 3979-3985.
15. For recent synthetic approaches to sphinganines, see: (a) Ndakala, A. J.; Hashemzadeh, M.; So, R. C.; Howell, A. R. Org. Lett. 2002, 4, 1719-1722; (b) Hertweck, C.; Sebek, P.; Svatos, A. Synlett 2001, 1965-1967; (c) He, L.; Byun, H.-S.; Bittman, R. J. Org. Chem. 2000, 65, 7618-7626; (d) Fernandes, R. A.; Kumar, P. Eur. J. Org. Chem. 2000, 3447-3449; (e) Azuma, H.; Tamagaki, S.; Ogino, K. J. Org. Chem. 2000, 65, 3538-3541; (f) Fernandes, R. A.; Kumar, P. Tetrahedron: Asymmetry 1999, 10, 4797-4802; (g) Villard, R.; Fotiadu, F.; Buono, G. Tetrahedron: Asymmetry 1998, 9, 607-611; (h) Hoffman, R. V.; Tao, J. J. Org. Chem. 1998, 63, 3979-3985.
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20. All compounds displayed satisfactory spectroscopic (NMR, IR) and analytical data (combustion analysis or HRMS) consistent with their structure.
21. 1H NMR spectra.
22. Careful chelation controlled addition of vinyl lithium reagents to aminoaldehydes generated in situ from DIBAL/TRIBAL in non-ether solvents have been reported to proceed with high (>20:1) selectivity: (a) Sames, D.; Polt, R. J. Org. Chem. 1994, 59, 4596-4601. See also: (b) Angle, S. R.; Henry, R. H. J. Org. Chem. 1997, 62, 8549-8552; (c) Ibuka, T.; Habashita, H.; Otaka, A.; Fujii, N.; Oguchi, Y.; Uyehara, T.; Yamamoto, Y. J. Org. Chem. 1991, 56, 4370-4382.
23. Careful chelation controlled addition of vinyl lithium reagents to aminoaldehydes generated in situ from DIBAL/TRIBAL in non-ether solvents have been reported to proceed with high (>20:1) selectivity: (a) Sames, D.; Polt, R. J. Org. Chem. 1994, 59, 4596-4601. See also: (b) Angle, S. R.; Henry, R. H. J. Org. Chem. 1997, 62, 8549-8552; (c) Ibuka, T.; Habashita, H.; Otaka, A.; Fujii, N.; Oguchi, Y.; Uyehara, T.; Yamamoto, Y. J. Org. Chem. 1991, 56, 4370-4382.
24. Careful chelation controlled addition of vinyl lithium reagents to aminoaldehydes generated in situ from DIBAL/TRIBAL in non-ether solvents have been reported to proceed with high (>20:1) selectivity: (a) Sames, D.; Polt, R. J. Org. Chem. 1994, 59, 4596-4601. See also: (b) Angle, S. R.; Henry, R. H. J. Org. Chem. 1997, 62, 8549-8552; (c) Ibuka, T.; Habashita, H.; Otaka, A.; Fujii, N.; Oguchi, Y.; Uyehara, T.; Yamamoto, Y. J. Org. Chem. 1991, 56, 4370-4382.
25. 2 according to the literature procedure: Millar J.G., Underhill E.W. J. Org. Chem. 51:1986;4726-4728.
26. Spectral characterization and optical rotation were consistent with that reported in the literature. See Ref. 3f and references cited therein.