Enantioselective modification of the Pomeranz-Fritsch-Bobbitt synthesis of tetrahydroisoquinoline alkaloids synthesis of (-)-salsolidine and (-)-carnegine

Tetrahedron Asymmetry

Volumn 11, Issue 11, 2000, Pages 2359-2366

  Gluszyńska, Agata ^a   Rozwadowska, Maria D ^a  

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

CARNEGINE; IMINE; METHYLLITHIUM; ORGANOLITHIUM COMPOUND; SALSOLIDINE; TETRAHYDROISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; CONTROLLED STUDY; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; MASS SPECTROMETRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; TECHNIQUE; THIN LAYER CHROMATOGRAPHY;

EID: 0343184004     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00196-8     Document Type: Article

References (29)

1. Bobbitt, J. M.; McNew Kiely, J.; Khanna, K. L.; Eberman, R. J. Org. chem. 1965, 30, 2247-2250.
2. (a) Shamma, M. The Isoquinoline Alkaloids, Chemistry and Pharmacology; Academic Press: New York, 1972.
3. (b) Shamma, M.; Moniot, L. Isoquinoline Alkaloid Research 1972- 1977; Plenum Press: New York, 1978.
4. Bobbitt, J. M.; Steinfeld, A. S.; Weisgraber, K. H.; Dutta, S. J. Org. Chem. 1969, 34, 2478-2479.
5. Birch, A. J.; Jackson, A. H.; Shannon, P. V. R. J. Chem. Soc., Perkin Trans. 1 1974, 2190-2194.
6. Yamada, K.; Takeda, M.; Itoh, N.; Ohtsuka, H.; Tsunashima, A.; Iwakuma, T. Chem. Pharm. Bull. 1982, 30, 3197-3201.
7. Carillo, L.; Badia, D.; Dominguez, E.; Vicario, J.; Tellitu, I. J. Org. Chem. 1997, 62, 6716-6721.
8. (a) Garcia, A.; Castedo, L.; Dominguez, D. Synlett 1993, 271-272.
9. (b) Garcia, A.; Castedo, L.; Dominguez, D. Tetrahedron Lett. 1993, 34, 1797-1798.
10. (a) Hirsenkorn, R. Tetrahedron Lett. 1990, 31, 7591-7594.
11. (b) Hirsenkorn, R. Tetrahedron Lett. 1991, 32, 1775-1779.
12. Ponzo, V. L.; Kaufman, T. S. Tetrahedron Lett. 1995, 36, 9105-9108.
13. Kaufman, T. S. Synth. Commun. 1993, 23, 473-476.
14. Birch, A. J.; Jackson, A. H.; Shannon, P. V. R. J. Chem. Soc., Perkin Trans. 1 1974, 2185-2190.
15. Rozwadowska, M. D. Heterocycles 1994, 39, 903-931.
16. Denmark, S. E.; Nicaise, O. J. C. J. Chem. Soc., Chem. Commun. 1996, 999-1004.
17. Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895-1946.
18. Gant, T. G.; Meyers, A. I. Tetrahedron 1997, 50, 2297-2360.
19. Meyers, A. I. J. Heterocyclic Chem. 1998, 35, 991-1002.
20. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 859-875.
21. (a) Rozwadowska, M. D. Tetrahedron: Asymmetry 1998, 9, 1615-1618.
22. (b) Brózda, D.; Chrzanowska, M.; Gluszyńska, A.; Rozwadowska, M. D. Tetrahedron: Asymmetry 1999, 10, 4791-4796.
23. (a) Rozwadowska, M. D. Tetrahedron: Asymmetry 1993, 4, 1619-1624.
24. (b) Fiedorow, P.; Ratajczak-Sitarz, M.; Rozwadowska, M. D.; Rozwadowski, Z. J. Mol. Struct. 1998, 442, 65-70.
25. Kamata, K.; Agata, I. J. Org. Chem. 1998, 63, 3113-3116.
26. (a) Tomioka, K.; Inoue, I.; Shindo, M.; Koga, K. Tetrahedron Lett. 1991, 32, 3095-3098.
27. (b) Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron 1994, 50, 4429-4438.
28. Bussche-Hunnefeld, C.; Beck, A. K.; Seebach, D. Helvetica Chim. Acta 1992, 75, 438-441.
29. Battersby, A. R.; Edwards, T. P. J. Chem. Soc. 1960, 1214-1221.