A new synthesis of chiral aminoalkyloxazolecarboxylate esters from isoxazol-5(2H)-ones: The synthesis of almazoles A and B

Tetrahedron Letters

Volumn 39, Issue 30, 1998, Pages 5405-5408

  Khalafy, Jabbar ^a,b   Svensson, Carina E ^a   Prager, Rolf H ^a   Williams, Craig M ^a  

^a FLINDERS UNIVERSITY   (Australia)

^b URMIA UNIVERSITY   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

ALMAZOLE A; ALMAZOLE B; ESTER; ISOXAZOLE DERIVATIVE; NATURAL PRODUCT; OXAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CHIRALITY; DRUG SYNTHESIS; PHOTOLYSIS; RACEMIC MIXTURE;

EID: 0032560711     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01014-4     Document Type: Article

References (24)

1. 1. Foster, M.P., Concepcion, G.P., Caraan, G.B., Ireland, C.M., J. Org. Chem. 1992, 57, 6671.
2. 2. Aguilar, E.; Meyers, A.I., Tetrahedron Lett., 1994, 35 , 2477; Turchi, I.J. ed., Oxazoles, Wiley-Interscience, NY, 1986; Evans, D. A.; Minster, D. K.; Jordis, U.; Hecht, S. M.; Mazzu, A. L.; Meyers, A. I., J. Org. Chem..,1979, 44, 497; Connel, R.; Scaro, F.; Helquist, P.; Akermark, B.,Tetrahedron Lett., 1986,17, 5559; Connel, R.; Tebbe, M.; Gangloff, A.; Helquist, P.; Akermark, B., Tetrahedron, 1993, 49 , 5445; Evans, D. A.; Gage, J.R.; Leighton, J. L., J. Am. Chem. Soc. , 1992, 114 , 9434; Wipf, P.; Miller, P., J. Org. Chem., 1993, 58 , 3604 ; Shapiro, R., J. Org. Chem. , 1993, 58 , 5759 ; Wipf, P., Chem. Rev., 1995, 95 , 2115; Knight, D.W., Pattenden, G., Rippon, D.E., Synlett, 1990, 1, 36.
3. 2. Aguilar, E.; Meyers, A.I., Tetrahedron Lett., 1994, 35 , 2477; Turchi, I.J. ed., Oxazoles, Wiley-Interscience, NY, 1986; Evans, D. A.; Minster, D. K.; Jordis, U.; Hecht, S. M.; Mazzu, A. L.; Meyers, A. I., J. Org. Chem..,1979, 44, 497; Connel, R.; Scaro, F.; Helquist, P.; Akermark, B.,Tetrahedron Lett., 1986,17, 5559; Connel, R.; Tebbe, M.; Gangloff, A.; Helquist, P.; Akermark, B., Tetrahedron, 1993, 49 , 5445; Evans, D. A.; Gage, J.R.; Leighton, J. L., J. Am. Chem. Soc. , 1992, 114 , 9434; Wipf, P.; Miller, P., J. Org. Chem., 1993, 58 , 3604 ; Shapiro, R., J. Org. Chem. , 1993, 58 , 5759 ; Wipf, P., Chem. Rev., 1995, 95 , 2115; Knight, D.W., Pattenden, G., Rippon, D.E., Synlett, 1990, 1, 36.
4. 2. Aguilar, E.; Meyers, A.I., Tetrahedron Lett., 1994, 35 , 2477; Turchi, I.J. ed., Oxazoles, Wiley-Interscience, NY, 1986; Evans, D. A.; Minster, D. K.; Jordis, U.; Hecht, S. M.; Mazzu, A. L.; Meyers, A. I., J. Org. Chem..,1979, 44, 497; Connel, R.; Scaro, F.; Helquist, P.; Akermark, B.,Tetrahedron Lett., 1986,17, 5559; Connel, R.; Tebbe, M.; Gangloff, A.; Helquist, P.; Akermark, B., Tetrahedron, 1993, 49 , 5445; Evans, D. A.; Gage, J.R.; Leighton, J. L., J. Am. Chem. Soc. , 1992, 114 , 9434; Wipf, P.; Miller, P., J. Org. Chem., 1993, 58 , 3604 ; Shapiro, R., J. Org. Chem. , 1993, 58 , 5759 ; Wipf, P., Chem. Rev., 1995, 95 , 2115; Knight, D.W., Pattenden, G., Rippon, D.E., Synlett, 1990, 1, 36.
5. 2. Aguilar, E.; Meyers, A.I., Tetrahedron Lett., 1994, 35 , 2477; Turchi, I.J. ed., Oxazoles, Wiley-Interscience, NY, 1986; Evans, D. A.; Minster, D. K.; Jordis, U.; Hecht, S. M.; Mazzu, A. L.; Meyers, A. I., J. Org. Chem..,1979, 44, 497; Connel, R.; Scaro, F.; Helquist, P.; Akermark, B.,Tetrahedron Lett., 1986,17, 5559; Connel, R.; Tebbe, M.; Gangloff, A.; Helquist, P.; Akermark, B., Tetrahedron, 1993, 49 , 5445; Evans, D. A.; Gage, J.R.; Leighton, J. L., J. Am. Chem. Soc. , 1992, 114 , 9434; Wipf, P.; Miller, P., J. Org. Chem., 1993, 58 , 3604 ; Shapiro, R., J. Org. Chem. , 1993, 58 , 5759 ; Wipf, P., Chem. Rev., 1995, 95 , 2115; Knight, D.W., Pattenden, G., Rippon, D.E., Synlett, 1990, 1, 36.
6. 2. Aguilar, E.; Meyers, A.I., Tetrahedron Lett., 1994, 35 , 2477; Turchi, I.J. ed., Oxazoles, Wiley-Interscience, NY, 1986; Evans, D. A.; Minster, D. K.; Jordis, U.; Hecht, S. M.; Mazzu, A. L.; Meyers, A. I., J. Org. Chem..,1979, 44, 497; Connel, R.; Scaro, F.; Helquist, P.; Akermark, B.,Tetrahedron Lett., 1986,17, 5559; Connel, R.; Tebbe, M.; Gangloff, A.; Helquist, P.; Akermark, B., Tetrahedron, 1993, 49 , 5445; Evans, D. A.; Gage, J.R.; Leighton, J. L., J. Am. Chem. Soc. , 1992, 114 , 9434; Wipf, P.; Miller, P., J. Org. Chem., 1993, 58 , 3604 ; Shapiro, R., J. Org. Chem. , 1993, 58 , 5759 ; Wipf, P., Chem. Rev., 1995, 95 , 2115; Knight, D.W., Pattenden, G., Rippon, D.E., Synlett, 1990, 1, 36.
7. 2. Aguilar, E.; Meyers, A.I., Tetrahedron Lett., 1994, 35 , 2477; Turchi, I.J. ed., Oxazoles, Wiley-Interscience, NY, 1986; Evans, D. A.; Minster, D. K.; Jordis, U.; Hecht, S. M.; Mazzu, A. L.; Meyers, A. I., J. Org. Chem..,1979, 44, 497; Connel, R.; Scaro, F.; Helquist, P.; Akermark, B.,Tetrahedron Lett., 1986,17, 5559; Connel, R.; Tebbe, M.; Gangloff, A.; Helquist, P.; Akermark, B., Tetrahedron, 1993, 49 , 5445; Evans, D. A.; Gage, J.R.; Leighton, J. L., J. Am. Chem. Soc. , 1992, 114 , 9434; Wipf, P.; Miller, P., J. Org. Chem., 1993, 58 , 3604 ; Shapiro, R., J. Org. Chem. , 1993, 58 , 5759 ; Wipf, P., Chem. Rev., 1995, 95 , 2115; Knight, D.W., Pattenden, G., Rippon, D.E., Synlett, 1990, 1, 36.
8. 2. Aguilar, E.; Meyers, A.I., Tetrahedron Lett., 1994, 35 , 2477; Turchi, I.J. ed., Oxazoles, Wiley-Interscience, NY, 1986; Evans, D. A.; Minster, D. K.; Jordis, U.; Hecht, S. M.; Mazzu, A. L.; Meyers, A. I., J. Org. Chem..,1979, 44, 497; Connel, R.; Scaro, F.; Helquist, P.; Akermark, B.,Tetrahedron Lett., 1986,17, 5559; Connel, R.; Tebbe, M.; Gangloff, A.; Helquist, P.; Akermark, B., Tetrahedron, 1993, 49 , 5445; Evans, D. A.; Gage, J.R.; Leighton, J. L., J. Am. Chem. Soc. , 1992, 114 , 9434; Wipf, P.; Miller, P., J. Org. Chem., 1993, 58 , 3604 ; Shapiro, R., J. Org. Chem. , 1993, 58 , 5759 ; Wipf, P., Chem. Rev., 1995, 95 , 2115; Knight, D.W., Pattenden, G., Rippon, D.E., Synlett, 1990, 1, 36.
9. 2. Aguilar, E.; Meyers, A.I., Tetrahedron Lett., 1994, 35 , 2477; Turchi, I.J. ed., Oxazoles, Wiley-Interscience, NY, 1986; Evans, D. A.; Minster, D. K.; Jordis, U.; Hecht, S. M.; Mazzu, A. L.; Meyers, A. I., J. Org. Chem..,1979, 44, 497; Connel, R.; Scaro, F.; Helquist, P.; Akermark, B.,Tetrahedron Lett., 1986,17, 5559; Connel, R.; Tebbe, M.; Gangloff, A.; Helquist, P.; Akermark, B., Tetrahedron, 1993, 49 , 5445; Evans, D. A.; Gage, J.R.; Leighton, J. L., J. Am. Chem. Soc. , 1992, 114 , 9434; Wipf, P.; Miller, P., J. Org. Chem., 1993, 58 , 3604 ; Shapiro, R., J. Org. Chem. , 1993, 58 , 5759 ; Wipf, P., Chem. Rev., 1995, 95 , 2115; Knight, D.W., Pattenden, G., Rippon, D.E., Synlett, 1990, 1, 36.
10. 2. Aguilar, E.; Meyers, A.I., Tetrahedron Lett., 1994, 35 , 2477; Turchi, I.J. ed., Oxazoles, Wiley-Interscience, NY, 1986; Evans, D. A.; Minster, D. K.; Jordis, U.; Hecht, S. M.; Mazzu, A. L.; Meyers, A. I., J. Org. Chem..,1979, 44, 497; Connel, R.; Scaro, F.; Helquist, P.; Akermark, B.,Tetrahedron Lett., 1986,17, 5559; Connel, R.; Tebbe, M.; Gangloff, A.; Helquist, P.; Akermark, B., Tetrahedron, 1993, 49 , 5445; Evans, D. A.; Gage, J.R.; Leighton, J. L., J. Am. Chem. Soc. , 1992, 114 , 9434; Wipf, P.; Miller, P., J. Org. Chem., 1993, 58 , 3604 ; Shapiro, R., J. Org. Chem. , 1993, 58 , 5759 ; Wipf, P., Chem. Rev., 1995, 95 , 2115; Knight, D.W., Pattenden, G., Rippon, D.E., Synlett, 1990, 1, 36.
11. 2. Aguilar, E.; Meyers, A.I., Tetrahedron Lett., 1994, 35 , 2477; Turchi, I.J. ed., Oxazoles, Wiley-Interscience, NY, 1986; Evans, D. A.; Minster, D. K.; Jordis, U.; Hecht, S. M.; Mazzu, A. L.; Meyers, A. I., J. Org. Chem..,1979, 44, 497; Connel, R.; Scaro, F.; Helquist, P.; Akermark, B.,Tetrahedron Lett., 1986,17, 5559; Connel, R.; Tebbe, M.; Gangloff, A.; Helquist, P.; Akermark, B., Tetrahedron, 1993, 49 , 5445; Evans, D. A.; Gage, J.R.; Leighton, J. L., J. Am. Chem. Soc. , 1992, 114 , 9434; Wipf, P.; Miller, P., J. Org. Chem., 1993, 58 , 3604 ; Shapiro, R., J. Org. Chem. , 1993, 58 , 5759 ; Wipf, P., Chem. Rev., 1995, 95 , 2115; Knight, D.W., Pattenden, G., Rippon, D.E., Synlett, 1990, 1, 36.
12. 3. Prager, R.H.; Smith, J.A.; Weber, B.; Williams, C.M., J.Chem. Soc., Perkin Trans.1, 1997, 2665.
13. 4. Prager, R.H.; Taylor, M.R.; Williams, C.M., J.Chem. Soc., Perkin Trans.1, 1997, 2673.
14. 5. Klausner, Y.S.; Bodansky, M., Synthesis, 1972, 453.
15. 6. Dale, J.A.; Dull, D.L.; Mosher, H.S., J.Org. Chem., 1969, 34, 2543..
16. 7. N'Diaye, I.; Guella, G.; Chiasera, G.; Mancini, F.; Pietra, F., Tetrahedron Lett., 1994, 35, 4827; Pietra, F.; Guella, G.; Mancini, I.; and N'Diaye, I., Helv. Chim. Acta, 1994, 77, 1999.
17. 7. N'Diaye, I.; Guella, G.; Chiasera, G.; Mancini, F.; Pietra, F., Tetrahedron Lett., 1994, 35, 4827; Pietra, F.; Guella, G.; Mancini, I.; and N'Diaye, I., Helv. Chim. Acta, 1994, 77, 1999.
18. 8. N'Diaye, I., Guella, G., Mancini, I., Pietra, K., Tetrahedron Lett., 1996, 37, 3049.
19. 9. Lewis, J.R., Nat. Prod. Rep., 1995, 12, 135 and references therein to earlier parts.
20. 10. Undheim, K.; Gacek, M., Tetrahedron, 1974, 30, 4233.
21. 11. Wolfe, S.; Hasan, S. K., Can. J. Chem., 1970, 48, 3572.
22. 12. Fleming, I.; Loreto, A.M.; Wallace, I.H.M.; Michael, J.P., J. Chem. Soc., Perkin Trans. 1, 1986, 349.
23. 13. Weinreb, S.M.; Levin, J. I.; Turos, E., Synth. Commun., 1982, 12, 989.
24. -1.