Regioselective lithiation of chiral 3-acylamino-2-alkylquinazolin-4(3H)- ones: Application in synthesis

Synthesis

Volumn , Issue 13, 2004, Pages 2121-2130

  Smith, Keith ^a   El Hiti, Gamal A ^a   Abdel Megeed, Mohamed F ^b  

^a SWANSEA UNIVERSITY   (United Kingdom)

^b Tanta University   (Egypt)

Author keywords

Asymmetric induction; Diastereotopism; Dilithio reagent; Lithiation; Quinazolin 4(3H) ones

Indexed keywords

CARBON; DERIVATIVES; LITHIUM; SUBSTITUTION REACTIONS;

REFLUX; REGIOISELECTIVE LITHIATION;

ORGANIC COMPOUNDS;

2 (1 DIPHENYLHYDROXYMETHYLPROPYL) 3 (2 PHENOXYBUTYRYLAMINO)QUINAZOLIN 4(3H) ONE; 2 (1 DIPHENYLHYDROXYMETHYLPROPYL) 3 (2 PHENOXYPROPIONYLAMINO)QUINAZOLIN 4(3H) ONE; 2 (1 ETHYL 2 HYDROXY 2 PHENYLPROPYL) 3 (2 PHENOXYBUTYRYLAMINO)QUINAZOLIN 4(3H) ONE; 2 (1 ETHYL 2 HYDROXY 2 PHENYLPROPYL) 3 (2 PHENOXYPROPIONYLAMINO)QUINAZOLIN 4(3H) ONE; 2 (1 PHENYLHYDROXYMETHYLPROPYL) 3 (2 PHENOXYBUTYRYLAMINO)QUINAZOLIN 4(3H) ONE; 2 (1 PHENYLHYDROXYMETHYLPROPYL) 3 (2 PHENOXYPROPIONYLAMINO)QUINAZOLIN 4(3H) ONE; 2 (1,2 DIMETHYL 2 HYDROXYBUTYL) 3 (2 PHENYLBUTYRYLAMINO)QUINAZOLIN 4(3H) ONE; 2 (2 HYDROXY 1 METHYL 2 PHENYLETHYL) 3 (2 PHENOXYBUTYRYLAMINO)QUINAZOLIN 4(3H) ONE; 2 (2 HYDROXY 1 METHYL 2 PHENYLETHYL) 3 (2 PHENOXYPROPIONYLAMINO)QUINAZOLIN 4(3H) ONE; 2 (2 HYDROXY 1 METHYL 2 PHENYLPROPYL) 3 (2 PHENOXYBUTYRYLAMINO)QUINAZOLIN 4(3H) ONE; 2 (2 HYDROXY 1 METHYL 2 PHENYLPROPYL) 3 (2 PHENOXYPROPIONYLAMINO)QUINAZOLIN 4(3H) ONE; 2 (2,2 DIPHENYL 2 HYDROXY 1 METHYLETHYL) 3 (2 PHENOXYBUTYRYLAMINO)QUINAZOLIN 4(3H) ONE; 2 (2,2 DIPHENYL 2 HYDROXY 1 METHYLETHYL) 3 (2 PHENOXYPROPIONYLAMINO)QUINAZOLIN 4(3H) ONE; 2 (2,2 DIPHENYL 2 HYDROXY 1 METHYLETHYL) 3 (2 PHENYLBUTYRYLAMINO)QUINAZOLIN 4(3H) ONE; 2 (2,2 DIPHENYL 2 HYDROXY 1 METHYLETHYL) 3 [2 (1 NAPHTHALENE)PROPIONYLAMINO]QUINAZOLIN 4(3H) ONE; 2 ETHYL 3 (2 PHENOXYBUTYRYLAMINO)QUINAZOLIN 4(3H) ONE; 2 ETHYL 3 (2 PHENOXYPROPIONYLAMINO)QUINAZOLIN 4(3H) ONE; 2 ETHYL 3 (2 PHENYLBUTYRYLAMINO)QUINAZOLIN 4(3H) ONE; 2 ETHYL 3 [2 (1 NAPHTHALENE)PROPIONYLAMINO]QUINAZOLIN 4(3H) ONE; 2 PROPYL 3 (2 PHENOXYBUTYRYLAMINO)QUINAZOLIN 4(3H) ONE; 2 PROPYL 3 (2 PHENOXYPROPIONYLAMINO)QUINAZOLIN 4(3H) ONE; LITHIUM DERIVATIVE; LITHIUM DIISOPROPYLAMIDE; QUINAZOLINE DERIVATIVE; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHIRALITY; CRYSTAL STRUCTURE; DIASTEREOISOMER; LITHIATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 4544333635     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-829169     Document Type: Article

References (52)

1. (a) Beak, P.; Zajdel, W. J.; Reitz, D. B. Chem. Rev. 1984, 84, 471.
2. (b) Snieckus, V. Chem. Rev. 1990, 90, 879.
3. (c) El-Hiti, G. A. Heterocycles 2000, 53, 1839.
4. (d) Mongin, F.; Quéguiner, G. Tetrahedron 2001, 57, 4059.
5. (e) Turck, A.; Plé, N.; Mongin, F.; Quéguiner, G. Tetrahedron 2001, 57, 4489.
6. (f) Anctil, E. J.-G.; Snieckus, V. J. Organomet. Chem. 2002, 653, 150.
7. (g) Smith, K.; El-Hiti, G. A. Curr. Org. Synth. 2004, 1, in press.
8. (h) Chinchilla, R.; Nájera, C.; Yus, M. Chem. Rev. 2004, 104, 2667.
9. See for example: (a) Choppin, S.; Gros, P.; Fort, Y. Org. Lett. 2000, 2, 803. (b) Kondo, Y.; Asai, M.; Miura, T.; Uchiyama, M.; Sakamoto, T. Org. Lett. 2001, 3, 13. (c) Rebstock, A.-S.; Mongin, F.; Trécourt, F.; Quéguiner, G. Tetrahedron Lett. 2002, 43, 767. (d) Rhonnstad, P.; Wensbo, D. Tetrahedron Lett. 2002, 43, 3137. (e) Mukherjee, C.; De, A. Synlett 2002, 325. (f) Cuperly, D.; Gros, P.; Fort, Y. J. Org. Chem. 2002, 67, 238. (g) Gros, P.; Louërat, F.; Fort, Y. Org. Lett. 2002, 4, 175. (h) Toudic, F.; Plé, N.; Turck, A.; Quéguiner, G. Tetrahedron 2002, 58, 238. (i) Bunch, L.; Krogsgaard-Larsen, P.; Madsen, U. J. Org. Chem. 2002, 67, 2375. (j) Katritzky, A. R.; Manju, K.; Steel, P. J. J. Org. Chem. 2003, 68, 407. (k) Gros, P.; Choppin, S.; Fort, Y. J. Org. Chem. 2003, 68, 2243. (l) El-Hiti, G. A. Synthesis 2004, 363. (m) Cabiddu, M. C.; Cabiddu, S.; Cadoni, E.; De Montis, S.; Fattuoni, C.; Melis, S. Tetrahedron 2004, 60, 3915.
10. See for example: (a) Choppin, S.; Gros, P.; Fort, Y. Org. Lett. 2000, 2, 803. (b) Kondo, Y.; Asai, M.; Miura, T.; Uchiyama, M.; Sakamoto, T. Org. Lett. 2001, 3, 13. (c) Rebstock, A.-S.; Mongin, F.; Trécourt, F.; Quéguiner, G. Tetrahedron Lett. 2002, 43, 767. (d) Rhonnstad, P.; Wensbo, D. Tetrahedron Lett. 2002, 43, 3137. (e) Mukherjee, C.; De, A. Synlett 2002, 325. (f) Cuperly, D.; Gros, P.; Fort, Y. J. Org. Chem. 2002, 67, 238. (g) Gros, P.; Louërat, F.; Fort, Y. Org. Lett. 2002, 4, 175. (h) Toudic, F.; Plé, N.; Turck, A.; Quéguiner, G. Tetrahedron 2002, 58, 238. (i) Bunch, L.; Krogsgaard-Larsen, P.; Madsen, U. J. Org. Chem. 2002, 67, 2375. (j) Katritzky, A. R.; Manju, K.; Steel, P. J. J. Org. Chem. 2003, 68, 407. (k) Gros, P.; Choppin, S.; Fort, Y. J. Org. Chem. 2003, 68, 2243. (l) El-Hiti, G. A. Synthesis 2004, 363. (m) Cabiddu, M. C.; Cabiddu, S.; Cadoni, E.; De Montis, S.; Fattuoni, C.; Melis, S. Tetrahedron 2004, 60, 3915.
11. See for example: (a) Choppin, S.; Gros, P.; Fort, Y. Org. Lett. 2000, 2, 803. (b) Kondo, Y.; Asai, M.; Miura, T.; Uchiyama, M.; Sakamoto, T. Org. Lett. 2001, 3, 13. (c) Rebstock, A.-S.; Mongin, F.; Trécourt, F.; Quéguiner, G. Tetrahedron Lett. 2002, 43, 767. (d) Rhonnstad, P.; Wensbo, D. Tetrahedron Lett. 2002, 43, 3137. (e) Mukherjee, C.; De, A. Synlett 2002, 325. (f) Cuperly, D.; Gros, P.; Fort, Y. J. Org. Chem. 2002, 67, 238. (g) Gros, P.; Louërat, F.; Fort, Y. Org. Lett. 2002, 4, 175. (h) Toudic, F.; Plé, N.; Turck, A.; Quéguiner, G. Tetrahedron 2002, 58, 238. (i) Bunch, L.; Krogsgaard-Larsen, P.; Madsen, U. J. Org. Chem. 2002, 67, 2375. (j) Katritzky, A. R.; Manju, K.; Steel, P. J. J. Org. Chem. 2003, 68, 407. (k) Gros, P.; Choppin, S.; Fort, Y. J. Org. Chem. 2003, 68, 2243. (l) El-Hiti, G. A. Synthesis 2004, 363. (m) Cabiddu, M. C.; Cabiddu, S.; Cadoni, E.; De Montis, S.; Fattuoni, C.; Melis, S. Tetrahedron 2004, 60, 3915.
12. See for example: (a) Choppin, S.; Gros, P.; Fort, Y. Org. Lett. 2000, 2, 803. (b) Kondo, Y.; Asai, M.; Miura, T.; Uchiyama, M.; Sakamoto, T. Org. Lett. 2001, 3, 13. (c) Rebstock, A.-S.; Mongin, F.; Trécourt, F.; Quéguiner, G. Tetrahedron Lett. 2002, 43, 767. (d) Rhonnstad, P.; Wensbo, D. Tetrahedron Lett. 2002, 43, 3137. (e) Mukherjee, C.; De, A. Synlett 2002, 325. (f) Cuperly, D.; Gros, P.; Fort, Y. J. Org. Chem. 2002, 67, 238. (g) Gros, P.; Louërat, F.; Fort, Y. Org. Lett. 2002, 4, 175. (h) Toudic, F.; Plé, N.; Turck, A.; Quéguiner, G. Tetrahedron 2002, 58, 238. (i) Bunch, L.; Krogsgaard-Larsen, P.; Madsen, U. J. Org. Chem. 2002, 67, 2375. (j) Katritzky, A. R.; Manju, K.; Steel, P. J. J. Org. Chem. 2003, 68, 407. (k) Gros, P.; Choppin, S.; Fort, Y. J. Org. Chem. 2003, 68, 2243. (l) El-Hiti, G. A. Synthesis 2004, 363. (m) Cabiddu, M. C.; Cabiddu, S.; Cadoni, E.; De Montis, S.; Fattuoni, C.; Melis, S. Tetrahedron 2004, 60, 3915.
13. See for example: (a) Choppin, S.; Gros, P.; Fort, Y. Org. Lett. 2000, 2, 803. (b) Kondo, Y.; Asai, M.; Miura, T.; Uchiyama, M.; Sakamoto, T. Org. Lett. 2001, 3, 13. (c) Rebstock, A.-S.; Mongin, F.; Trécourt, F.; Quéguiner, G. Tetrahedron Lett. 2002, 43, 767. (d) Rhonnstad, P.; Wensbo, D. Tetrahedron Lett. 2002, 43, 3137. (e) Mukherjee, C.; De, A. Synlett 2002, 325. (f) Cuperly, D.; Gros, P.; Fort, Y. J. Org. Chem. 2002, 67, 238. (g) Gros, P.; Louërat, F.; Fort, Y. Org. Lett. 2002, 4, 175. (h) Toudic, F.; Plé, N.; Turck, A.; Quéguiner, G. Tetrahedron 2002, 58, 238. (i) Bunch, L.; Krogsgaard-Larsen, P.; Madsen, U. J. Org. Chem. 2002, 67, 2375. (j) Katritzky, A. R.; Manju, K.; Steel, P. J. J. Org. Chem. 2003, 68, 407. (k) Gros, P.; Choppin, S.; Fort, Y. J. Org. Chem. 2003, 68, 2243. (l) El-Hiti, G. A. Synthesis 2004, 363. (m) Cabiddu, M. C.; Cabiddu, S.; Cadoni, E.; De Montis, S.; Fattuoni, C.; Melis, S. Tetrahedron 2004, 60, 3915.
14. See for example: (a) Choppin, S.; Gros, P.; Fort, Y. Org. Lett. 2000, 2, 803. (b) Kondo, Y.; Asai, M.; Miura, T.; Uchiyama, M.; Sakamoto, T. Org. Lett. 2001, 3, 13. (c) Rebstock, A.-S.; Mongin, F.; Trécourt, F.; Quéguiner, G. Tetrahedron Lett. 2002, 43, 767. (d) Rhonnstad, P.; Wensbo, D. Tetrahedron Lett. 2002, 43, 3137. (e) Mukherjee, C.; De, A. Synlett 2002, 325. (f) Cuperly, D.; Gros, P.; Fort, Y. J. Org. Chem. 2002, 67, 238. (g) Gros, P.; Louërat, F.; Fort, Y. Org. Lett. 2002, 4, 175. (h) Toudic, F.; Plé, N.; Turck, A.; Quéguiner, G. Tetrahedron 2002, 58, 238. (i) Bunch, L.; Krogsgaard-Larsen, P.; Madsen, U. J. Org. Chem. 2002, 67, 2375. (j) Katritzky, A. R.; Manju, K.; Steel, P. J. J. Org. Chem. 2003, 68, 407. (k) Gros, P.; Choppin, S.; Fort, Y. J. Org. Chem. 2003, 68, 2243. (l) El-Hiti, G. A. Synthesis 2004, 363. (m) Cabiddu, M. C.; Cabiddu, S.; Cadoni, E.; De Montis, S.; Fattuoni, C.; Melis, S. Tetrahedron 2004, 60, 3915.
15. See for example: (a) Choppin, S.; Gros, P.; Fort, Y. Org. Lett. 2000, 2, 803. (b) Kondo, Y.; Asai, M.; Miura, T.; Uchiyama, M.; Sakamoto, T. Org. Lett. 2001, 3, 13. (c) Rebstock, A.-S.; Mongin, F.; Trécourt, F.; Quéguiner, G. Tetrahedron Lett. 2002, 43, 767. (d) Rhonnstad, P.; Wensbo, D. Tetrahedron Lett. 2002, 43, 3137. (e) Mukherjee, C.; De, A. Synlett 2002, 325. (f) Cuperly, D.; Gros, P.; Fort, Y. J. Org. Chem. 2002, 67, 238. (g) Gros, P.; Louërat, F.; Fort, Y. Org. Lett. 2002, 4, 175. (h) Toudic, F.; Plé, N.; Turck, A.; Quéguiner, G. Tetrahedron 2002, 58, 238. (i) Bunch, L.; Krogsgaard-Larsen, P.; Madsen, U. J. Org. Chem. 2002, 67, 2375. (j) Katritzky, A. R.; Manju, K.; Steel, P. J. J. Org. Chem. 2003, 68, 407. (k) Gros, P.; Choppin, S.; Fort, Y. J. Org. Chem. 2003, 68, 2243. (l) El-Hiti, G. A. Synthesis 2004, 363. (m) Cabiddu, M. C.; Cabiddu, S.; Cadoni, E.; De Montis, S.; Fattuoni, C.; Melis, S. Tetrahedron 2004, 60, 3915.
16. See for example: (a) Choppin, S.; Gros, P.; Fort, Y. Org. Lett. 2000, 2, 803. (b) Kondo, Y.; Asai, M.; Miura, T.; Uchiyama, M.; Sakamoto, T. Org. Lett. 2001, 3, 13. (c) Rebstock, A.-S.; Mongin, F.; Trécourt, F.; Quéguiner, G. Tetrahedron Lett. 2002, 43, 767. (d) Rhonnstad, P.; Wensbo, D. Tetrahedron Lett. 2002, 43, 3137. (e) Mukherjee, C.; De, A. Synlett 2002, 325. (f) Cuperly, D.; Gros, P.; Fort, Y. J. Org. Chem. 2002, 67, 238. (g) Gros, P.; Louërat, F.; Fort, Y. Org. Lett. 2002, 4, 175. (h) Toudic, F.; Plé, N.; Turck, A.; Quéguiner, G. Tetrahedron 2002, 58, 238. (i) Bunch, L.; Krogsgaard-Larsen, P.; Madsen, U. J. Org. Chem. 2002, 67, 2375. (j) Katritzky, A. R.; Manju, K.; Steel, P. J. J. Org. Chem. 2003, 68, 407. (k) Gros, P.; Choppin, S.; Fort, Y. J. Org. Chem. 2003, 68, 2243. (l) El-Hiti, G. A. Synthesis 2004, 363. (m) Cabiddu, M. C.; Cabiddu, S.; Cadoni, E.; De Montis, S.; Fattuoni, C.; Melis, S. Tetrahedron 2004, 60, 3915.
17. See for example: (a) Choppin, S.; Gros, P.; Fort, Y. Org. Lett. 2000, 2, 803. (b) Kondo, Y.; Asai, M.; Miura, T.; Uchiyama, M.; Sakamoto, T. Org. Lett. 2001, 3, 13. (c) Rebstock, A.-S.; Mongin, F.; Trécourt, F.; Quéguiner, G. Tetrahedron Lett. 2002, 43, 767. (d) Rhonnstad, P.; Wensbo, D. Tetrahedron Lett. 2002, 43, 3137. (e) Mukherjee, C.; De, A. Synlett 2002, 325. (f) Cuperly, D.; Gros, P.; Fort, Y. J. Org. Chem. 2002, 67, 238. (g) Gros, P.; Louërat, F.; Fort, Y. Org. Lett. 2002, 4, 175. (h) Toudic, F.; Plé, N.; Turck, A.; Quéguiner, G. Tetrahedron 2002, 58, 238. (i) Bunch, L.; Krogsgaard-Larsen, P.; Madsen, U. J. Org. Chem. 2002, 67, 2375. (j) Katritzky, A. R.; Manju, K.; Steel, P. J. J. Org. Chem. 2003, 68, 407. (k) Gros, P.; Choppin, S.; Fort, Y. J. Org. Chem. 2003, 68, 2243. (l) El-Hiti, G. A. Synthesis 2004, 363. (m) Cabiddu, M. C.; Cabiddu, S.; Cadoni, E.; De Montis, S.; Fattuoni, C.; Melis, S. Tetrahedron 2004, 60, 3915.
18. See for example: (a) Choppin, S.; Gros, P.; Fort, Y. Org. Lett. 2000, 2, 803. (b) Kondo, Y.; Asai, M.; Miura, T.; Uchiyama, M.; Sakamoto, T. Org. Lett. 2001, 3, 13. (c) Rebstock, A.-S.; Mongin, F.; Trécourt, F.; Quéguiner, G. Tetrahedron Lett. 2002, 43, 767. (d) Rhonnstad, P.; Wensbo, D. Tetrahedron Lett. 2002, 43, 3137. (e) Mukherjee, C.; De, A. Synlett 2002, 325. (f) Cuperly, D.; Gros, P.; Fort, Y. J. Org. Chem. 2002, 67, 238. (g) Gros, P.; Louërat, F.; Fort, Y. Org. Lett. 2002, 4, 175. (h) Toudic, F.; Plé, N.; Turck, A.; Quéguiner, G. Tetrahedron 2002, 58, 238. (i) Bunch, L.; Krogsgaard-Larsen, P.; Madsen, U. J. Org. Chem. 2002, 67, 2375. (j) Katritzky, A. R.; Manju, K.; Steel, P. J. J. Org. Chem. 2003, 68, 407. (k) Gros, P.; Choppin, S.; Fort, Y. J. Org. Chem. 2003, 68, 2243. (l) El-Hiti, G. A. Synthesis 2004, 363. (m) Cabiddu, M. C.; Cabiddu, S.; Cadoni, E.; De Montis, S.; Fattuoni, C.; Melis, S. Tetrahedron 2004, 60, 3915.
19. See for example: (a) Choppin, S.; Gros, P.; Fort, Y. Org. Lett. 2000, 2, 803. (b) Kondo, Y.; Asai, M.; Miura, T.; Uchiyama, M.; Sakamoto, T. Org. Lett. 2001, 3, 13. (c) Rebstock, A.-S.; Mongin, F.; Trécourt, F.; Quéguiner, G. Tetrahedron Lett. 2002, 43, 767. (d) Rhonnstad, P.; Wensbo, D. Tetrahedron Lett. 2002, 43, 3137. (e) Mukherjee, C.; De, A. Synlett 2002, 325. (f) Cuperly, D.; Gros, P.; Fort, Y. J. Org. Chem. 2002, 67, 238. (g) Gros, P.; Louërat, F.; Fort, Y. Org. Lett. 2002, 4, 175. (h) Toudic, F.; Plé, N.; Turck, A.; Quéguiner, G. Tetrahedron 2002, 58, 238. (i) Bunch, L.; Krogsgaard-Larsen, P.; Madsen, U. J. Org. Chem. 2002, 67, 2375. (j) Katritzky, A. R.; Manju, K.; Steel, P. J. J. Org. Chem. 2003, 68, 407. (k) Gros, P.; Choppin, S.; Fort, Y. J. Org. Chem. 2003, 68, 2243. (l) El-Hiti, G. A. Synthesis 2004, 363. (m) Cabiddu, M. C.; Cabiddu, S.; Cadoni, E.; De Montis, S.; Fattuoni, C.; Melis, S. Tetrahedron 2004, 60, 3915.
20. See for example: (a) Choppin, S.; Gros, P.; Fort, Y. Org. Lett. 2000, 2, 803. (b) Kondo, Y.; Asai, M.; Miura, T.; Uchiyama, M.; Sakamoto, T. Org. Lett. 2001, 3, 13. (c) Rebstock, A.-S.; Mongin, F.; Trécourt, F.; Quéguiner, G. Tetrahedron Lett. 2002, 43, 767. (d) Rhonnstad, P.; Wensbo, D. Tetrahedron Lett. 2002, 43, 3137. (e) Mukherjee, C.; De, A. Synlett 2002, 325. (f) Cuperly, D.; Gros, P.; Fort, Y. J. Org. Chem. 2002, 67, 238. (g) Gros, P.; Louërat, F.; Fort, Y. Org. Lett. 2002, 4, 175. (h) Toudic, F.; Plé, N.; Turck, A.; Quéguiner, G. Tetrahedron 2002, 58, 238. (i) Bunch, L.; Krogsgaard-Larsen, P.; Madsen, U. J. Org. Chem. 2002, 67, 2375. (j) Katritzky, A. R.; Manju, K.; Steel, P. J. J. Org. Chem. 2003, 68, 407. (k) Gros, P.; Choppin, S.; Fort, Y. J. Org. Chem. 2003, 68, 2243. (l) El-Hiti, G. A. Synthesis 2004, 363. (m) Cabiddu, M. C.; Cabiddu, S.; Cadoni, E.; De Montis, S.; Fattuoni, C.; Melis, S. Tetrahedron 2004, 60, 3915.
21. See for example: (a) Choppin, S.; Gros, P.; Fort, Y. Org. Lett. 2000, 2, 803. (b) Kondo, Y.; Asai, M.; Miura, T.; Uchiyama, M.; Sakamoto, T. Org. Lett. 2001, 3, 13. (c) Rebstock, A.-S.; Mongin, F.; Trécourt, F.; Quéguiner, G. Tetrahedron Lett. 2002, 43, 767. (d) Rhonnstad, P.; Wensbo, D. Tetrahedron Lett. 2002, 43, 3137. (e) Mukherjee, C.; De, A. Synlett 2002, 325. (f) Cuperly, D.; Gros, P.; Fort, Y. J. Org. Chem. 2002, 67, 238. (g) Gros, P.; Louërat, F.; Fort, Y. Org. Lett. 2002, 4, 175. (h) Toudic, F.; Plé, N.; Turck, A.; Quéguiner, G. Tetrahedron 2002, 58, 238. (i) Bunch, L.; Krogsgaard-Larsen, P.; Madsen, U. J. Org. Chem. 2002, 67, 2375. (j) Katritzky, A. R.; Manju, K.; Steel, P. J. J. Org. Chem. 2003, 68, 407. (k) Gros, P.; Choppin, S.; Fort, Y. J. Org. Chem. 2003, 68, 2243. (l) El-Hiti, G. A. Synthesis 2004, 363. (m) Cabiddu, M. C.; Cabiddu, S.; Cadoni, E.; De Montis, S.; Fattuoni, C.; Melis, S. Tetrahedron 2004, 60, 3915.
22. Murray, T. P.; Hay, J. V.; Protlock, D. E.; Wolfe, J. F. J. Org. Chem. 1974, 39, 595.
23. Rathman, T. L.; Sleevi, M. C.; Krafft, M. F.; Wolfe, J. F. J. Org. Chem. 1980, 45, 2169.
24. Smith, K.; El-Hiti, G. A.; Abdel-Megeed, M. F.; Abdo, M. A. Collect. Czech. Chem. Commun. 1999, 64, 515.
25. Smith, K.; El-Hiti, G. A.; Abdel-Megeed, M. F.; Abdo, M. A. J. Org. Chem. 1996, 61, 656.
26. El-Hiti, G. A. Monatsh. Chem. 2004, 135, 323.
27. Smith, K.; El-Hiti, G. A.; Abdel-Megeed, M. F.; Abdo, M. A. J. Org. Chem. 1996, 61, 647.
28. Smith, K.; El-Hiti, G. A.; Abdo, M. A.; Abdel-Megeed, M. F. J. Chem. Soc., Perkin Trans. 1 1995, 1029.
29. Plé, N.; Turck, A.; Chapoulaud, V.; Quéguiner, G. Tetrahedron 1997, 53, 2871.
30. Dai, X.; Virgil, S. Tetrahedron: Asymmetry 1999, 10, 25.
31. Chapoulaud, V. G.; Salliot, I.; Plé, N.; Turck, A.; Quéguiner, G. Tetrahedron 1999, 55, 5389.
32. See for example: (a) Honda, G.; Tabata, M.; Tsuda, M. Planta Med. 1979, 37, 172. (b) Johne, S. Prog. Drug Res. 1982, 26, 259. (c) Johne, S. Alkaloids 1986, 29, 99. (d) Schlecker, R.; Treiber, H. J.; Behl, B.; Hofmann, H. P. Ger. Pat., 4241563, 1994; Chem. Abstr. 1994, 121, 230787. (e) Barker, A. J. Eur. Pat., 635498, 1995; Chem. Abstr. 1995, 722, 214099. (f) Barker, A. J.; Johnstine, C. PCT Int Appl, WO 30044, 1997; Chem. Abstr. 1995, 127, 220671. (g) Hour, M.-J.; Huang, L.-J.; Kuo, S.-C.; Xia, Y.; Bastow, K.; Nakanishi, Y.; Hamel, E.; Lee, K.-H. J. Med. Chem. 2000, 43, 4479. (h) Ho, N.; Harapanhalli, R. S.; Dahman, B. A.; Chen, K.; Wang, K. Bioconjugate Chem. 2002, 13, 357.
33. See for example: (a) Honda, G.; Tabata, M.; Tsuda, M. Planta Med. 1979, 37, 172. (b) Johne, S. Prog. Drug Res. 1982, 26, 259. (c) Johne, S. Alkaloids 1986, 29, 99. (d) Schlecker, R.; Treiber, H. J.; Behl, B.; Hofmann, H. P. Ger. Pat., 4241563, 1994; Chem. Abstr. 1994, 121, 230787. (e) Barker, A. J. Eur. Pat., 635498, 1995; Chem. Abstr. 1995, 722, 214099. (f) Barker, A. J.; Johnstine, C. PCT Int Appl, WO 30044, 1997; Chem. Abstr. 1995, 127, 220671. (g) Hour, M.-J.; Huang, L.-J.; Kuo, S.-C.; Xia, Y.; Bastow, K.; Nakanishi, Y.; Hamel, E.; Lee, K.-H. J. Med. Chem. 2000, 43, 4479. (h) Ho, N.; Harapanhalli, R. S.; Dahman, B. A.; Chen, K.; Wang, K. Bioconjugate Chem. 2002, 13, 357.
34. See for example: (a) Honda, G.; Tabata, M.; Tsuda, M. Planta Med. 1979, 37, 172. (b) Johne, S. Prog. Drug Res. 1982, 26, 259. (c) Johne, S. Alkaloids 1986, 29, 99. (d) Schlecker, R.; Treiber, H. J.; Behl, B.; Hofmann, H. P. Ger. Pat., 4241563, 1994; Chem. Abstr. 1994, 121, 230787. (e) Barker, A. J. Eur. Pat., 635498, 1995; Chem. Abstr. 1995, 722, 214099. (f) Barker, A. J.; Johnstine, C. PCT Int Appl, WO 30044, 1997; Chem. Abstr. 1995, 127, 220671. (g) Hour, M.-J.; Huang, L.-J.; Kuo, S.-C.; Xia, Y.; Bastow, K.; Nakanishi, Y.; Hamel, E.; Lee, K.-H. J. Med. Chem. 2000, 43, 4479. (h) Ho, N.; Harapanhalli, R. S.; Dahman, B. A.; Chen, K.; Wang, K. Bioconjugate Chem. 2002, 13, 357.
35. See for example: (a) Honda, G.; Tabata, M.; Tsuda, M. Planta Med. 1979, 37, 172. (b) Johne, S. Prog. Drug Res. 1982, 26, 259. (c) Johne, S. Alkaloids 1986, 29, 99. (d) Schlecker, R.; Treiber, H. J.; Behl, B.; Hofmann, H. P. Ger. Pat., 4241563, 1994; Chem. Abstr. 1994, 121, 230787. (e) Barker, A. J. Eur. Pat., 635498, 1995; Chem. Abstr. 1995, 722, 214099. (f) Barker, A. J.; Johnstine, C. PCT Int Appl, WO 30044, 1997; Chem. Abstr. 1995, 127, 220671. (g) Hour, M.-J.; Huang, L.-J.; Kuo, S.-C.; Xia, Y.; Bastow, K.; Nakanishi, Y.; Hamel, E.; Lee, K.-H. J. Med. Chem. 2000, 43, 4479. (h) Ho, N.; Harapanhalli, R. S.; Dahman, B. A.; Chen, K.; Wang, K. Bioconjugate Chem. 2002, 13, 357.
36. See for example: (a) Honda, G.; Tabata, M.; Tsuda, M. Planta Med. 1979, 37, 172. (b) Johne, S. Prog. Drug Res. 1982, 26, 259. (c) Johne, S. Alkaloids 1986, 29, 99. (d) Schlecker, R.; Treiber, H. J.; Behl, B.; Hofmann, H. P. Ger. Pat., 4241563, 1994; Chem. Abstr. 1994, 121, 230787. (e) Barker, A. J. Eur. Pat., 635498, 1995; Chem. Abstr. 1995, 722, 214099. (f) Barker, A. J.; Johnstine, C. PCT Int Appl, WO 30044, 1997; Chem. Abstr. 1995, 127, 220671. (g) Hour, M.-J.; Huang, L.-J.; Kuo, S.-C.; Xia, Y.; Bastow, K.; Nakanishi, Y.; Hamel, E.; Lee, K.-H. J. Med. Chem. 2000, 43, 4479. (h) Ho, N.; Harapanhalli, R. S.; Dahman, B. A.; Chen, K.; Wang, K. Bioconjugate Chem. 2002, 13, 357.
37. See for example: (a) Honda, G.; Tabata, M.; Tsuda, M. Planta Med. 1979, 37, 172. (b) Johne, S. Prog. Drug Res. 1982, 26, 259. (c) Johne, S. Alkaloids 1986, 29, 99. (d) Schlecker, R.; Treiber, H. J.; Behl, B.; Hofmann, H. P. Ger. Pat., 4241563, 1994; Chem. Abstr. 1994, 121, 230787. (e) Barker, A. J. Eur. Pat., 635498, 1995; Chem. Abstr. 1995, 722, 214099. (f) Barker, A. J.; Johnstine, C. PCT Int Appl, WO 30044, 1997; Chem. Abstr. 1995, 127, 220671. (g) Hour, M.-J.; Huang, L.-J.; Kuo, S.-C.; Xia, Y.; Bastow, K.; Nakanishi, Y.; Hamel, E.; Lee, K.-H. J. Med. Chem. 2000, 43, 4479. (h) Ho, N.; Harapanhalli, R. S.; Dahman, B. A.; Chen, K.; Wang, K. Bioconjugate Chem. 2002, 13, 357.
38. See for example: (a) Honda, G.; Tabata, M.; Tsuda, M. Planta Med. 1979, 37, 172. (b) Johne, S. Prog. Drug Res. 1982, 26, 259. (c) Johne, S. Alkaloids 1986, 29, 99. (d) Schlecker, R.; Treiber, H. J.; Behl, B.; Hofmann, H. P. Ger. Pat., 4241563, 1994; Chem. Abstr. 1994, 121, 230787. (e) Barker, A. J. Eur. Pat., 635498, 1995; Chem. Abstr. 1995, 722, 214099. (f) Barker, A. J.; Johnstine, C. PCT Int Appl, WO 30044, 1997; Chem. Abstr. 1995, 127, 220671. (g) Hour, M.-J.; Huang, L.-J.; Kuo, S.-C.; Xia, Y.; Bastow, K.; Nakanishi, Y.; Hamel, E.; Lee, K.-H. J. Med. Chem. 2000, 43, 4479. (h) Ho, N.; Harapanhalli, R. S.; Dahman, B. A.; Chen, K.; Wang, K. Bioconjugate Chem. 2002, 13, 357.
39. See for example: (a) Honda, G.; Tabata, M.; Tsuda, M. Planta Med. 1979, 37, 172. (b) Johne, S. Prog. Drug Res. 1982, 26, 259. (c) Johne, S. Alkaloids 1986, 29, 99. (d) Schlecker, R.; Treiber, H. J.; Behl, B.; Hofmann, H. P. Ger. Pat., 4241563, 1994; Chem. Abstr. 1994, 121, 230787. (e) Barker, A. J. Eur. Pat., 635498, 1995; Chem. Abstr. 1995, 722, 214099. (f) Barker, A. J.; Johnstine, C. PCT Int Appl, WO 30044, 1997; Chem. Abstr. 1995, 127, 220671. (g) Hour, M.-J.; Huang, L.-J.; Kuo, S.-C.; Xia, Y.; Bastow, K.; Nakanishi, Y.; Hamel, E.; Lee, K.-H. J. Med. Chem. 2000, 43, 4479. (h) Ho, N.; Harapanhalli, R. S.; Dahman, B. A.; Chen, K.; Wang, K. Bioconjugate Chem. 2002, 13, 357.
40. See for example: (a) Smith, K.; El-Hiti, G. A.; Hamilton, A. J. Chem. Soc., Perkin Trans. 1 1998, 4041. (b) Smith, K.; El-Hiti, G. A.; Pritchard, G. J.; Hamilton, A. J. Chem. Soc., Perkin Trans. 1 1999, 2299. (c) Smith, K.; El-Hiti, G. A.; Shukla, A. P. J. Chem. Soc., Perkin Trans. 1 1999, 2305. (d) Smith, K.; El-Hiti, G. A.; Abdel-Megeed, M. F. Russ. J. Org. Chem. 2003, 39, 430. (e) Smith, K.; El-Hiti, G. A.; Hawes, A. C. Synthesis 2003, 2047. (f) Smith, K.; El-Hiti, G. A.; Mahgoub, S. A. Synthesis 2003, 2345. (g) El-Hiti, G. A. Synthesis 2003, 2799.
41. See for example: (a) Smith, K.; El-Hiti, G. A.; Hamilton, A. J. Chem. Soc., Perkin Trans. 1 1998, 4041. (b) Smith, K.; El-Hiti, G. A.; Pritchard, G. J.; Hamilton, A. J. Chem. Soc., Perkin Trans. 1 1999, 2299. (c) Smith, K.; El-Hiti, G. A.; Shukla, A. P. J. Chem. Soc., Perkin Trans. 1 1999, 2305. (d) Smith, K.; El-Hiti, G. A.; Abdel-Megeed, M. F. Russ. J. Org. Chem. 2003, 39, 430. (e) Smith, K.; El-Hiti, G. A.; Hawes, A. C. Synthesis 2003, 2047. (f) Smith, K.; El-Hiti, G. A.; Mahgoub, S. A. Synthesis 2003, 2345. (g) El-Hiti, G. A. Synthesis 2003, 2799.
42. See for example: (a) Smith, K.; El-Hiti, G. A.; Hamilton, A. J. Chem. Soc., Perkin Trans. 1 1998, 4041. (b) Smith, K.; El-Hiti, G. A.; Pritchard, G. J.; Hamilton, A. J. Chem. Soc., Perkin Trans. 1 1999, 2299. (c) Smith, K.; El-Hiti, G. A.; Shukla, A. P. J. Chem. Soc., Perkin Trans. 1 1999, 2305. (d) Smith, K.; El-Hiti, G. A.; Abdel-Megeed, M. F. Russ. J. Org. Chem. 2003, 39, 430. (e) Smith, K.; El-Hiti, G. A.; Hawes, A. C. Synthesis 2003, 2047. (f) Smith, K.; El-Hiti, G. A.; Mahgoub, S. A. Synthesis 2003, 2345. (g) El-Hiti, G. A. Synthesis 2003, 2799.
43. See for example: (a) Smith, K.; El-Hiti, G. A.; Hamilton, A. J. Chem. Soc., Perkin Trans. 1 1998, 4041. (b) Smith, K.; El-Hiti, G. A.; Pritchard, G. J.; Hamilton, A. J. Chem. Soc., Perkin Trans. 1 1999, 2299. (c) Smith, K.; El-Hiti, G. A.; Shukla, A. P. J. Chem. Soc., Perkin Trans. 1 1999, 2305. (d) Smith, K.; El-Hiti, G. A.; Abdel-Megeed, M. F. Russ. J. Org. Chem. 2003, 39, 430. (e) Smith, K.; El-Hiti, G. A.; Hawes, A. C. Synthesis 2003, 2047. (f) Smith, K.; El-Hiti, G. A.; Mahgoub, S. A. Synthesis 2003, 2345. (g) El-Hiti, G. A. Synthesis 2003, 2799.
44. See for example: (a) Smith, K.; El-Hiti, G. A.; Hamilton, A. J. Chem. Soc., Perkin Trans. 1 1998, 4041. (b) Smith, K.; El-Hiti, G. A.; Pritchard, G. J.; Hamilton, A. J. Chem. Soc., Perkin Trans. 1 1999, 2299. (c) Smith, K.; El-Hiti, G. A.; Shukla, A. P. J. Chem. Soc., Perkin Trans. 1 1999, 2305. (d) Smith, K.; El-Hiti, G. A.; Abdel-Megeed, M. F. Russ. J. Org. Chem. 2003, 39, 430. (e) Smith, K.; El-Hiti, G. A.; Hawes, A. C. Synthesis 2003, 2047. (f) Smith, K.; El-Hiti, G. A.; Mahgoub, S. A. Synthesis 2003, 2345. (g) El-Hiti, G. A. Synthesis 2003, 2799.
45. See for example: (a) Smith, K.; El-Hiti, G. A.; Hamilton, A. J. Chem. Soc., Perkin Trans. 1 1998, 4041. (b) Smith, K.; El-Hiti, G. A.; Pritchard, G. J.; Hamilton, A. J. Chem. Soc., Perkin Trans. 1 1999, 2299. (c) Smith, K.; El-Hiti, G. A.; Shukla, A. P. J. Chem. Soc., Perkin Trans. 1 1999, 2305. (d) Smith, K.; El-Hiti, G. A.; Abdel-Megeed, M. F. Russ. J. Org. Chem. 2003, 39, 430. (e) Smith, K.; El-Hiti, G. A.; Hawes, A. C. Synthesis 2003, 2047. (f) Smith, K.; El-Hiti, G. A.; Mahgoub, S. A. Synthesis 2003, 2345. (g) El-Hiti, G. A. Synthesis 2003, 2799.
46. See for example: (a) Smith, K.; El-Hiti, G. A.; Hamilton, A. J. Chem. Soc., Perkin Trans. 1 1998, 4041. (b) Smith, K.; El-Hiti, G. A.; Pritchard, G. J.; Hamilton, A. J. Chem. Soc., Perkin Trans. 1 1999, 2299. (c) Smith, K.; El-Hiti, G. A.; Shukla, A. P. J. Chem. Soc., Perkin Trans. 1 1999, 2305. (d) Smith, K.; El-Hiti, G. A.; Abdel-Megeed, M. F. Russ. J. Org. Chem. 2003, 39, 430. (e) Smith, K.; El-Hiti, G. A.; Hawes, A. C. Synthesis 2003, 2047. (f) Smith, K.; El-Hiti, G. A.; Mahgoub, S. A. Synthesis 2003, 2345. (g) El-Hiti, G. A. Synthesis 2003, 2799.
47. Sammour, A.; Selim, M.; El Kasaby, M.; Abdalla, M. Acta Chim. (Budapest) 1973, 78, 293; Chem. Abstr. 1973, 79, 137061.
48. Sammour, A.; Selim, M.; El Kasaby, M.; Abdalla, M. Acta Chim. (Budapest) 1973, 78, 293; Chem. Abstr. 1973, 79, 137061.
49. Essawy, A.; El-Hashash, M. A.; El-Gendy, A. M.; Hamad, M. M. M. Indian J. Chem.: Sect. B 1982, 21, 593.
50. El-Hiti, G. A. Spectrosc. Lett. 1999, 32, 671.
51. Vogel's Textbook of Practical Organic Chemistry, 5th ed.; Longman: Harlow, 1989.
52. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon: Oxford, 1988.