Preparation of chiral hexahydroquinolizinones and tetrahydroindolizinones by regio- and diastereoselective sonochemical cyclization of chiral dihydropyridines

Tetrahedron Letters

Volumn 37, Issue 10, 1996, Pages 1599-1602

  Raussou, Sabine ^a   Urbain, Nicolas ^a   Mangeney, Pierre ^a   Alexakis, Alexandre ^a   Platzer, Nicole ^b  

^a CNRS   (France)

^b Laboratoire de Chimie Organique Biologique   (France)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLIZINE DERIVATIVE; QUINOLIZINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0029877506     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00076-7     Document Type: Article

References (11)

1. Mangeney, P.; Gosmini, R.; Raussou, S.; Commerçon, M.; Alexakis, A. J.Org. Chem. 1994, 59, 1877-1888.
2. For synthesis of quinolizidine and indolizidine alkaloids see: Michael, J.P. Natur. Prod. Rep., 1995, 12, 535-552. For synthesis of racemic tetrahydroindolizinones and hexahydroquinolizinones Uyehara, T.; Suzuki, I.; Yamamoto, Y. Tetrahedron Lett. 1990, 31, 3753-3756.
3. For synthesis of quinolizidine and indolizidine alkaloids see: Michael, J.P. Natur. Prod. Rep., 1995, 12, 535-552. For synthesis of racemic tetrahydroindolizinones and hexahydroquinolizinones Uyehara, T.; Suzuki, I.; Yamamoto, Y. Tetrahedron Lett. 1990, 31, 3753-3756.
4. Beckwith, A.L.J.; Westwood, S.W. Tetrahedron 1989, 45, 5269. Beckwith, A.L.J.; Joseph, S.P.; Mayadunne, R.T.A. J.Org. Chem. 1993, 58, 4198-4199. Ishibashi, H.; Kameoka, C.; Sato, T.; Ikeda, M. Synlett 1994, 445-446. Lee, E.; Kang, T. S.; Joo, B.J.; Tae, J.S.; Li, K. S.; Chung, C. K. Tetrahedron Lett. 1995, 36, 417-420.
5. Beckwith, A.L.J.; Westwood, S.W. Tetrahedron 1989, 45, 5269. Beckwith, A.L.J.; Joseph, S.P.; Mayadunne, R.T.A. J.Org. Chem. 1993, 58, 4198-4199. Ishibashi, H.; Kameoka, C.; Sato, T.; Ikeda, M. Synlett 1994, 445-446. Lee, E.; Kang, T. S.; Joo, B.J.; Tae, J.S.; Li, K. S.; Chung, C. K. Tetrahedron Lett. 1995, 36, 417-420.
6. Beckwith, A.L.J.; Westwood, S.W. Tetrahedron 1989, 45, 5269. Beckwith, A.L.J.; Joseph, S.P.; Mayadunne, R.T.A. J.Org. Chem. 1993, 58, 4198-4199. Ishibashi, H.; Kameoka, C.; Sato, T.; Ikeda, M. Synlett 1994, 445-446. Lee, E.; Kang, T. S.; Joo, B.J.; Tae, J.S.; Li, K. S.; Chung, C. K. Tetrahedron Lett. 1995, 36, 417-420.
7. Beckwith, A.L.J.; Westwood, S.W. Tetrahedron 1989, 45, 5269. Beckwith, A.L.J.; Joseph, S.P.; Mayadunne, R.T.A. J.Org. Chem. 1993, 58, 4198-4199. Ishibashi, H.; Kameoka, C.; Sato, T.; Ikeda, M. Synlett 1994, 445-446. Lee, E.; Kang, T. S.; Joo, B.J.; Tae, J.S.; Li, K. S.; Chung, C. K. Tetrahedron Lett. 1995, 36, 417-420.
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10. Dupuis, C., Petrier, C.; Sarandeses, L.A.; Luche, J.L. Synth. comm., 1991, 21, 643-651.
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