A new highly efficient synthetic route to enantiopure 10-bromocamphor

Tetrahedron Asymmetry

Volumn 11, Issue 15, 2000, Pages 3059-3062

  Maroto, Beatriz Lora ^a   De La Moya Cerero, Santiago ^a   Martínez, Antonio García ^a   Fraile, Amelia García ^b   Vilar, Enrique Teso ^b  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b UNIVERSIDAD NACIONAL DE EDUCACIÓN A DISTANCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CAMPHOR DERIVATIVE;

ENANTIOMER; PRIORITY JOURNAL; SHORT SURVEY; STEREOSPECIFICITY; SYNTHESIS;

EID: 0034637187     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00279-2     Document Type: Article

References (24)

1. For a review, see: (a) Oppolzer, W. Tetrahedron 1987, 1969. Some recent examples are: (b) Davis, F. A.; Zhou, P.; Murphy, C. K.; Sundarababu, G.; Qi, H.; Han, W.; Przerlawski, R. M.; Chen, B.-C.; Carroll, P. J. J. Org. Chem. 1998, 63, 2273. Verdaguer, X.; Vázquez, J.; Fuster, G.; Bernardes-Génisson, V.; Greene, A. E.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 1998, 63, 7037. Ramón, D. J.; Yus, M. Tetrahedron Lett. 1998, 39, 1239. (e) Cermak, D. M.; Du, Y.; Wiemer, D. F. J. Org. Chem. 1999, 64, 388. (f) Node, M.; Nishide, K.; Shigeta, Y.; Shiraki, H.; Obata, K. J. Am. Chem. Soc. 2000, 122, 1927.
2. For a review, see: (a) Oppolzer, W. Tetrahedron 1987, 1969. Some recent examples are: (b) Davis, F. A.; Zhou, P.; Murphy, C. K.; Sundarababu, G.; Qi, H.; Han, W.; Przerlawski, R. M.; Chen, B.-C.; Carroll, P. J. J. Org. Chem. 1998, 63, 2273. Verdaguer, X.; Vázquez, J.; Fuster, G.; Bernardes-Génisson, V.; Greene, A. E.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 1998, 63, 7037. Ramón, D. J.; Yus, M. Tetrahedron Lett. 1998, 39, 1239. (e) Cermak, D. M.; Du, Y.; Wiemer, D. F. J. Org. Chem. 1999, 64, 388. (f) Node, M.; Nishide, K.; Shigeta, Y.; Shiraki, H.; Obata, K. J. Am. Chem. Soc. 2000, 122, 1927.
3. For a review, see: (a) Oppolzer, W. Tetrahedron 1987, 1969. Some recent examples are: (b) Davis, F. A.; Zhou, P.; Murphy, C. K.; Sundarababu, G.; Qi, H.; Han, W.; Przerlawski, R. M.; Chen, B.-C.; Carroll, P. J. J. Org. Chem. 1998, 63, 2273. Verdaguer, X.; Vázquez, J.; Fuster, G.; Bernardes-Génisson, V.; Greene, A. E.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 1998, 63, 7037. Ramón, D. J.; Yus, M. Tetrahedron Lett. 1998, 39, 1239. (e) Cermak, D. M.; Du, Y.; Wiemer, D. F. J. Org. Chem. 1999, 64, 388. (f) Node, M.; Nishide, K.; Shigeta, Y.; Shiraki, H.; Obata, K. J. Am. Chem. Soc. 2000, 122, 1927.
4. For a review, see: (a) Oppolzer, W. Tetrahedron 1987, 1969. Some recent examples are: (b) Davis, F. A.; Zhou, P.; Murphy, C. K.; Sundarababu, G.; Qi, H.; Han, W.; Przerlawski, R. M.; Chen, B.-C.; Carroll, P. J. J. Org. Chem. 1998, 63, 2273. Verdaguer, X.; Vázquez, J.; Fuster, G.; Bernardes-Génisson, V.; Greene, A. E.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 1998, 63, 7037. Ramón, D. J.; Yus, M. Tetrahedron Lett. 1998, 39, 1239. (e) Cermak, D. M.; Du, Y.; Wiemer, D. F. J. Org. Chem. 1999, 64, 388. (f) Node, M.; Nishide, K.; Shigeta, Y.; Shiraki, H.; Obata, K. J. Am. Chem. Soc. 2000, 122, 1927.
5. For a review, see: (a) Oppolzer, W. Tetrahedron 1987, 1969. Some recent examples are: (b) Davis, F. A.; Zhou, P.; Murphy, C. K.; Sundarababu, G.; Qi, H.; Han, W.; Przerlawski, R. M.; Chen, B.-C.; Carroll, P. J. J. Org. Chem. 1998, 63, 2273. Verdaguer, X.; Vázquez, J.; Fuster, G.; Bernardes-Génisson, V.; Greene, A. E.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 1998, 63, 7037. Ramón, D. J.; Yus, M. Tetrahedron Lett. 1998, 39, 1239. (e) Cermak, D. M.; Du, Y.; Wiemer, D. F. J. Org. Chem. 1999, 64, 388. (f) Node, M.; Nishide, K.; Shigeta, Y.; Shiraki, H.; Obata, K. J. Am. Chem. Soc. 2000, 122, 1927.
6. For a review, see: (a) Oppolzer, W. Tetrahedron 1987, 1969. Some recent examples are: (b) Davis, F. A.; Zhou, P.; Murphy, C. K.; Sundarababu, G.; Qi, H.; Han, W.; Przerlawski, R. M.; Chen, B.-C.; Carroll, P. J. J. Org. Chem. 1998, 63, 2273. Verdaguer, X.; Vázquez, J.; Fuster, G.; Bernardes-Génisson, V.; Greene, A. E.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 1998, 63, 7037. Ramón, D. J.; Yus, M. Tetrahedron Lett. 1998, 39, 1239. (e) Cermak, D. M.; Du, Y.; Wiemer, D. F. J. Org. Chem. 1999, 64, 388. (f) Node, M.; Nishide, K.; Shigeta, Y.; Shiraki, H.; Obata, K. J. Am. Chem. Soc. 2000, 122, 1927.
7. For examples on the total synthesis of (+)-zizaanoic acid, see: (a) Liu, H. J.; Chan, W. H. Can. J. Chem. 1982, 60, 1081; on the total synthesis of (+)-taxusin: (b) Paquette, L. A.; Zhao, M. J. Am. Chem. Soc. 1998, 120, 5203; on the total synthesis of taxol: Paquette, L. A.; Zhao, M.; Montgomery, F.; Zheng, Q.; Wang, T. Z.; Elmore, S.; Combrink, K.; Wang, H.-L.; Bailey, S.; Su, Z. Pure Appl. Chem. 1998, 70, 1449.
8. For examples on the total synthesis of (+)-zizaanoic acid, see: (a) Liu, H. J.; Chan, W. H. Can. J. Chem. 1982, 60, 1081; on the total synthesis of (+)-taxusin: (b) Paquette, L. A.; Zhao, M. J. Am. Chem. Soc. 1998, 120, 5203; on the total synthesis of taxol: Paquette, L. A.; Zhao, M.; Montgomery, F.; Zheng, Q.; Wang, T. Z.; Elmore, S.; Combrink, K.; Wang, H.-L.; Bailey, S.; Su, Z. Pure Appl. Chem. 1998, 70, 1449.
9. For examples on the total synthesis of (+)-zizaanoic acid, see: (a) Liu, H. J.; Chan, W. H. Can. J. Chem. 1982, 60, 1081; on the total synthesis of (+)-taxusin: (b) Paquette, L. A.; Zhao, M. J. Am. Chem. Soc. 1998, 120, 5203; on the total synthesis of taxol: Paquette, L. A.; Zhao, M.; Montgomery, F.; Zheng, Q.; Wang, T. Z.; Elmore, S.; Combrink, K.; Wang, H.-L.; Bailey, S.; Su, Z. Pure Appl. Chem. 1998, 70, 1449.
10. Reychler, A. Bull. Soc. Chim. Paris 1898, 19, 120.
11. Referred to C10-O: (a) Dallacker, F.; Alroggen, I.; Krings, H.; Laurs, B.; Lipp, M. Liebigs Ann. Chem. 1961, 647, 23. (b) Ikota, N.; Sakai, H.; Shibata, H.; Koga, K. Chem. Pharm. Bull. 1986, 34, 1050. Jingen, D.; Yaozong, J.; Guilan, L.; Lanjun, W.; Aiqiao, M. Synthesis 1991, 963. Ahn, K. H.; Lee, S.; Lim, A. J. Org. Chem. 1992, 57, 5065. (e) Ahn, K. H.; Lim, A.; Lee, S. Tetrahedron: Asymmetry 1993, 4, 2435. (f) Chu, Y.-Y.; Yu, C.-S.; Chen, C.-J.; Yang, K.-S.; Lian, J.-C.; Lin, C.-H.; Chen, K. J. Org. Chem. 1999, 64, 6993; referred to C10-N: (g) Schenone, P.; Tasca, A.; Bignardi, G.; Mosti, L. Eur. J. Med. Chem. 1975, 10, 412; referred to C10-halogen: (h) Oae, S.; Togo, H. Bull. Chem. Soc. Jpn. 1983, 56, 3802, see also Ref. 4a; referred to C10-Se: Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293; referred to C10-P: (j) Komarov, I. V.; Gorichko, M. V.; Kornilov, M. Tetrahedron: Asymmetry 1997, 8, 435.
12. Referred to C10-O: (a) Dallacker, F.; Alroggen, I.; Krings, H.; Laurs, B.; Lipp, M. Liebigs Ann. Chem. 1961, 647, 23. (b) Ikota, N.; Sakai, H.; Shibata, H.; Koga, K. Chem. Pharm. Bull. 1986, 34, 1050. Jingen, D.; Yaozong, J.; Guilan, L.; Lanjun, W.; Aiqiao, M. Synthesis 1991, 963. Ahn, K. H.; Lee, S.; Lim, A. J. Org. Chem. 1992, 57, 5065. (e) Ahn, K. H.; Lim, A.; Lee, S. Tetrahedron: Asymmetry 1993, 4, 2435. (f) Chu, Y.-Y.; Yu, C.-S.; Chen, C.-J.; Yang, K.-S.; Lian, J.-C.; Lin, C.-H.; Chen, K. J. Org. Chem. 1999, 64, 6993; referred to C10-N: (g) Schenone, P.; Tasca, A.; Bignardi, G.; Mosti, L. Eur. J. Med. Chem. 1975, 10, 412; referred to C10-halogen: (h) Oae, S.; Togo, H. Bull. Chem. Soc. Jpn. 1983, 56, 3802, see also Ref. 4a; referred to C10-Se: Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293; referred to C10-P: (j) Komarov, I. V.; Gorichko, M. V.; Kornilov, M. Tetrahedron: Asymmetry 1997, 8, 435.
13. Referred to C10-O: (a) Dallacker, F.; Alroggen, I.; Krings, H.; Laurs, B.; Lipp, M. Liebigs Ann. Chem. 1961, 647, 23. (b) Ikota, N.; Sakai, H.; Shibata, H.; Koga, K. Chem. Pharm. Bull. 1986, 34, 1050. Jingen, D.; Yaozong, J.; Guilan, L.; Lanjun, W.; Aiqiao, M. Synthesis 1991, 963. Ahn, K. H.; Lee, S.; Lim, A. J. Org. Chem. 1992, 57, 5065. (e) Ahn, K. H.; Lim, A.; Lee, S. Tetrahedron: Asymmetry 1993, 4, 2435. (f) Chu, Y.-Y.; Yu, C.-S.; Chen, C.-J.; Yang, K.-S.; Lian, J.-C.; Lin, C.-H.; Chen, K. J. Org. Chem. 1999, 64, 6993; referred to C10-N: (g) Schenone, P.; Tasca, A.; Bignardi, G.; Mosti, L. Eur. J. Med. Chem. 1975, 10, 412; referred to C10-halogen: (h) Oae, S.; Togo, H. Bull. Chem. Soc. Jpn. 1983, 56, 3802, see also Ref. 4a; referred to C10-Se: Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293; referred to C10-P: (j) Komarov, I. V.; Gorichko, M. V.; Kornilov, M. Tetrahedron: Asymmetry 1997, 8, 435.
14. Referred to C10-O: (a) Dallacker, F.; Alroggen, I.; Krings, H.; Laurs, B.; Lipp, M. Liebigs Ann. Chem. 1961, 647, 23. (b) Ikota, N.; Sakai, H.; Shibata, H.; Koga, K. Chem. Pharm. Bull. 1986, 34, 1050. Jingen, D.; Yaozong, J.; Guilan, L.; Lanjun, W.; Aiqiao, M. Synthesis 1991, 963. Ahn, K. H.; Lee, S.; Lim, A. J. Org. Chem. 1992, 57, 5065. (e) Ahn, K. H.; Lim, A.; Lee, S. Tetrahedron: Asymmetry 1993, 4, 2435. (f) Chu, Y.-Y.; Yu, C.-S.; Chen, C.-J.; Yang, K.-S.; Lian, J.-C.; Lin, C.-H.; Chen, K. J. Org. Chem. 1999, 64, 6993; referred to C10-N: (g) Schenone, P.; Tasca, A.; Bignardi, G.; Mosti, L. Eur. J. Med. Chem. 1975, 10, 412; referred to C10-halogen: (h) Oae, S.; Togo, H. Bull. Chem. Soc. Jpn. 1983, 56, 3802, see also Ref. 4a; referred to C10-Se: Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293; referred to C10-P: (j) Komarov, I. V.; Gorichko, M. V.; Kornilov, M. Tetrahedron: Asymmetry 1997, 8, 435.
15. Referred to C10-O: (a) Dallacker, F.; Alroggen, I.; Krings, H.; Laurs, B.; Lipp, M. Liebigs Ann. Chem. 1961, 647, 23. (b) Ikota, N.; Sakai, H.; Shibata, H.; Koga, K. Chem. Pharm. Bull. 1986, 34, 1050. Jingen, D.; Yaozong, J.; Guilan, L.; Lanjun, W.; Aiqiao, M. Synthesis 1991, 963. Ahn, K. H.; Lee, S.; Lim, A. J. Org. Chem. 1992, 57, 5065. (e) Ahn, K. H.; Lim, A.; Lee, S. Tetrahedron: Asymmetry 1993, 4, 2435. (f) Chu, Y.-Y.; Yu, C.-S.; Chen, C.-J.; Yang, K.-S.; Lian, J.-C.; Lin, C.-H.; Chen, K. J. Org. Chem. 1999, 64, 6993; referred to C10-N: (g) Schenone, P.; Tasca, A.; Bignardi, G.; Mosti, L. Eur. J. Med. Chem. 1975, 10, 412; referred to C10-halogen: (h) Oae, S.; Togo, H. Bull. Chem. Soc. Jpn. 1983, 56, 3802, see also Ref. 4a; referred to C10-Se: Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293; referred to C10-P: (j) Komarov, I. V.; Gorichko, M. V.; Kornilov, M. Tetrahedron: Asymmetry 1997, 8, 435.
16. Referred to C10-O: (a) Dallacker, F.; Alroggen, I.; Krings, H.; Laurs, B.; Lipp, M. Liebigs Ann. Chem. 1961, 647, 23. (b) Ikota, N.; Sakai, H.; Shibata, H.; Koga, K. Chem. Pharm. Bull. 1986, 34, 1050. Jingen, D.; Yaozong, J.; Guilan, L.; Lanjun, W.; Aiqiao, M. Synthesis 1991, 963. Ahn, K. H.; Lee, S.; Lim, A. J. Org. Chem. 1992, 57, 5065. (e) Ahn, K. H.; Lim, A.; Lee, S. Tetrahedron: Asymmetry 1993, 4, 2435. (f) Chu, Y.-Y.; Yu, C.-S.; Chen, C.-J.; Yang, K.-S.; Lian, J.-C.; Lin, C.-H.; Chen, K. J. Org. Chem. 1999, 64, 6993; referred to C10-N: (g) Schenone, P.; Tasca, A.; Bignardi, G.; Mosti, L. Eur. J. Med. Chem. 1975, 10, 412; referred to C10-halogen: (h) Oae, S.; Togo, H. Bull. Chem. Soc. Jpn. 1983, 56, 3802, see also Ref. 4a; referred to C10-Se: Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293; referred to C10-P: (j) Komarov, I. V.; Gorichko, M. V.; Kornilov, M. Tetrahedron: Asymmetry 1997, 8, 435.
17. Referred to C10-O: (a) Dallacker, F.; Alroggen, I.; Krings, H.; Laurs, B.; Lipp, M. Liebigs Ann. Chem. 1961, 647, 23. (b) Ikota, N.; Sakai, H.; Shibata, H.; Koga, K. Chem. Pharm. Bull. 1986, 34, 1050. Jingen, D.; Yaozong, J.; Guilan, L.; Lanjun, W.; Aiqiao, M. Synthesis 1991, 963. Ahn, K. H.; Lee, S.; Lim, A. J. Org. Chem. 1992, 57, 5065. (e) Ahn, K. H.; Lim, A.; Lee, S. Tetrahedron: Asymmetry 1993, 4, 2435. (f) Chu, Y.-Y.; Yu, C.-S.; Chen, C.-J.; Yang, K.-S.; Lian, J.-C.; Lin, C.-H.; Chen, K. J. Org. Chem. 1999, 64, 6993; referred to C10-N: (g) Schenone, P.; Tasca, A.; Bignardi, G.; Mosti, L. Eur. J. Med. Chem. 1975, 10, 412; referred to C10-halogen: (h) Oae, S.; Togo, H. Bull. Chem. Soc. Jpn. 1983, 56, 3802, see also Ref. 4a; referred to C10-Se: Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293; referred to C10-P: (j) Komarov, I. V.; Gorichko, M. V.; Kornilov, M. Tetrahedron: Asymmetry 1997, 8, 435.
18. Referred to C10-O: (a) Dallacker, F.; Alroggen, I.; Krings, H.; Laurs, B.; Lipp, M. Liebigs Ann. Chem. 1961, 647, 23. (b) Ikota, N.; Sakai, H.; Shibata, H.; Koga, K. Chem. Pharm. Bull. 1986, 34, 1050. Jingen, D.; Yaozong, J.; Guilan, L.; Lanjun, W.; Aiqiao, M. Synthesis 1991, 963. Ahn, K. H.; Lee, S.; Lim, A. J. Org. Chem. 1992, 57, 5065. (e) Ahn, K. H.; Lim, A.; Lee, S. Tetrahedron: Asymmetry 1993, 4, 2435. (f) Chu, Y.-Y.; Yu, C.-S.; Chen, C.-J.; Yang, K.-S.; Lian, J.-C.; Lin, C.-H.; Chen, K. J. Org. Chem. 1999, 64, 6993; referred to C10-N: (g) Schenone, P.; Tasca, A.; Bignardi, G.; Mosti, L. Eur. J. Med. Chem. 1975, 10, 412; referred to C10-halogen: (h) Oae, S.; Togo, H. Bull. Chem. Soc. Jpn. 1983, 56, 3802, see also Ref. 4a; referred to C10-Se: Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293; referred to C10-P: (j) Komarov, I. V.; Gorichko, M. V.; Kornilov, M. Tetrahedron: Asymmetry 1997, 8, 435.
19. Referred to C10-O: (a) Dallacker, F.; Alroggen, I.; Krings, H.; Laurs, B.; Lipp, M. Liebigs Ann. Chem. 1961, 647, 23. (b) Ikota, N.; Sakai, H.; Shibata, H.; Koga, K. Chem. Pharm. Bull. 1986, 34, 1050. Jingen, D.; Yaozong, J.; Guilan, L.; Lanjun, W.; Aiqiao, M. Synthesis 1991, 963. Ahn, K. H.; Lee, S.; Lim, A. J. Org. Chem. 1992, 57, 5065. (e) Ahn, K. H.; Lim, A.; Lee, S. Tetrahedron: Asymmetry 1993, 4, 2435. (f) Chu, Y.-Y.; Yu, C.-S.; Chen, C.-J.; Yang, K.-S.; Lian, J.-C.; Lin, C.-H.; Chen, K. J. Org. Chem. 1999, 64, 6993; referred to C10-N: (g) Schenone, P.; Tasca, A.; Bignardi, G.; Mosti, L. Eur. J. Med. Chem. 1975, 10, 412; referred to C10-halogen: (h) Oae, S.; Togo, H. Bull. Chem. Soc. Jpn. 1983, 56, 3802, see also Ref. 4a; referred to C10-Se: Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293; referred to C10-P: (j) Komarov, I. V.; Gorichko, M. V.; Kornilov, M. Tetrahedron: Asymmetry 1997, 8, 435.
20. Referred to C10-O: (a) Dallacker, F.; Alroggen, I.; Krings, H.; Laurs, B.; Lipp, M. Liebigs Ann. Chem. 1961, 647, 23. (b) Ikota, N.; Sakai, H.; Shibata, H.; Koga, K. Chem. Pharm. Bull. 1986, 34, 1050. Jingen, D.; Yaozong, J.; Guilan, L.; Lanjun, W.; Aiqiao, M. Synthesis 1991, 963. Ahn, K. H.; Lee, S.; Lim, A. J. Org. Chem. 1992, 57, 5065. (e) Ahn, K. H.; Lim, A.; Lee, S. Tetrahedron: Asymmetry 1993, 4, 2435. (f) Chu, Y.-Y.; Yu, C.-S.; Chen, C.-J.; Yang, K.-S.; Lian, J.-C.; Lin, C.-H.; Chen, K. J. Org. Chem. 1999, 64, 6993; referred to C10-N: (g) Schenone, P.; Tasca, A.; Bignardi, G.; Mosti, L. Eur. J. Med. Chem. 1975, 10, 412; referred to C10-halogen: (h) Oae, S.; Togo, H. Bull. Chem. Soc. Jpn. 1983, 56, 3802, see also Ref. 4a; referred to C10-Se: Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293; referred to C10-P: (j) Komarov, I. V.; Gorichko, M. V.; Kornilov, M. Tetrahedron: Asymmetry 1997, 8, 435.
21. For the enantiospecific synthesis of triflate 7, we have used a variant of the standard procedure previously described by us (García Martínez, A.; Teso Vilar, E.; Osío Barcina, J.; Rodríguez Herrero, M. E.; de la Moya Cerero, S.; Hanack, M.; Subramanian, L. R. Tetrahedron: Asymmetry 1993, 4, 2333), in which triisobutylamine was substituted as the non-nucleophilic base instead of the now commercially unavailable N,N-diisobutyl-2,4-dimethylpentylamine.
22. (a) García Martínez, A.; Teso Vilar, E.; García Fraile, A.; Ruano Franco, C.; Soto Salvador, J.; Subramanian, L. R.; Hanack, M. Synthesis 1987, 321:
23. (b) Enantiopure alcohol 8 has been previously described Libman, J.; Sprecher, M.; Mazur, Y. Tetrahedron 1969, 25, 1679.
24. 13C NMR, IR, MS and HRMS.