A highly efficient synthesis of the erythrina and B-homoerythrina skeleton by an AlMe3-mediated domino reaction

Angewandte Chemie - International Edition

Volumn 43, Issue 40, 2004, Pages 5391-5393

  El Bialy, Serry A A ^a   Braun, Holger ^a   Tietze, Lutz F ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Alkaloids; Amides; Domino reactions; Iminium ions; Lewis acids

Indexed keywords

ALKALINITY; ALUMINUM COMPOUNDS; BIOCHEMISTRY; SUBSTRATES;

DOMINO EFFECT; THREE STEP DOMINO REACTIONS;

SYNTHESIS (CHEMICAL);

ALKALOID; AMIDE; BETA HOMOERYTHRINA DERIVATIVE; ERYTHRINA DERIVATIVE; LEWIS ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; REACTION ANALYSIS; SYNTHESIS;

EID: 7244252980     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460283     Document Type: Article

References (43)

1. a) L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 134-170; Angew. Chem. Int. Ed. Engl. 1993, 32, 131-132;
2. a) L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 134-170; Angew. Chem. Int. Ed. Engl. 1993, 32, 131-132;
3. b) L. F. Tietze, Chem. Rev. 1996, 96, 115-136;
4. c) L. F. Tietze, A. Modi, Med. Chem. Res. 2000, 20, 301-322;
5. d) L. F. Tietze, F. Haunert in Stimulating Concepts in Chemistry (Eds.: M. Shibasaki, J. F. Stoddart, F. Vogtle), Wiley-VCH, Weinheim, 2000, p. 39-64;
6. e) H. Waldmann in Organic Synthesis Highlights II (Ed.: H. Waldmann), Wiley-VCH, Weinheim, 1995, p. 193-202;
7. f) G. Poli, G. Giambastiani, A. Heumann, Tetrahedron 2000, 56, 5959-5989.
8. a) A. Mondon, Tetrahedron 1963, 19, 911-917;
9. b) A. Mondon, Tetrahedron 1964, 20, 1729-1736;
10. c) A. Mondon, K. F. Hansen, Tetrahedron Lett. 1960, 5-8;
11. d) A. Mondon, H. Nestler, Angew. Chem. 1964, 76, 651-652; Angew. Chem. Int. Ed. Engl. 1964, 3, 588-589;
12. d) A. Mondon, H. Nestler, Angew. Chem. 1964, 76, 651-652; Angew. Chem. Int. Ed. Engl. 1964, 3, 588-589;
13. e) T. Sano, J. Toda, N. Kashiwaba, T. Oshima, Y. Tsuda, Chem. Pharm. Bull. 1987, 35, 479-500;
14. f) R. Ahmad-Schofiel, P. S. Mariano, J. Org. Chem. 1987, 52, 1478-1482;
15. g) H. Ishibashi, T. Sato, M. Takahashi, M. Hayashi, M. Ikeda, Heterocycles 1988, 27, 2787-2790;
16. h) B. Belleau, Can. J. Chem. 1957, 35, 651-662;
17. i) V. Prelog, A. Langemann, O. Rodig, M. Ternmah, Helv. Chim. Acta 1959, 42, 1301-1310;
18. j) S. Sugasawa, H. Yoshikawa, Chem. Pharm. Bull. 1960, 8, 290-293;
19. k) M. Müller, T. T. Grossnickle, V. Boekelheide, J. Am. Chem. Soc. 1959, 81, 3959-3963;
20. l) Y. Tsuda, T. Sano, Studies in Natural Products Chemistry, Vol. 3 (Ed.: A.-U. Rahman), Elsevier, Amsterdam, 1989, p. 455-493;
21. m) G. Stork, A. Brizzolara, H. Landesman, J. Szmuszkovicz, R. J. Terrell, J. Am. Chem. Soc. 1963, 85, 207-222;
22. n) M. E. Kuehne, W. G. Bornmann, W. H. Parsons, T. D. Spitzer, J. F. Blount, J. Zubieta, J. Org. Chem. 1988, 53, 3439-3450.
23. a) A. S. Chawla, V. K. Kapoor in Handbook of Plant and Fungal Toxicants (Ed.: J. F. D'Mello), CRC, London, 1997, 37-49;
24. b) D. S. Bhakuni, J. Indian Chem. Soc. 2002, 79, 203-210.
25. a) V. Boekelheide in Alkaloids, Vol. 7 (Ed.: R. H. F. Manske), Academic Press, New York, 1960, p. 201-227;
26. b) R. K. Hill in Alkaloids, Vol. 9 (Ed.: R. H. F. Manske), Academic Press, New York, 1967, p. 483-515;
27. S. F. Dyke, S. N. Quessy in The Alkaloids, Vol. 18 (Ed.: R. G. A. Rodrigo), Academic Press, New York, 1981, p. 1-98;
28. d) A. H. Jackson in Chemistry and Biology of Isoquinoline Alkaloids (Eds.: J. D. Phillipson, M. F. Margaret, M. H. Zenk), Springer, Berlin, 1985, p. 62-78;
29. e) A. S. Chawla, A. H. Jackson, Nat. Prod. Rep. 1984, 1, 371-373;
30. f) A. S. Chawla, A. H. Jackson, Nat. Prod. Rep. 1986, 3, 355-364;
31. g) K. W. Bentley, Nat. Prod. Rep. 1991, 8, 339-366;
32. h) K. W. Bentley, Nat. Prod. Rep., 1992, 9, 365-391;
33. i) K. W. Bentley, Nat. Prod. Rep. 1993, 10, 449-470;
34. j) K. W. Bentley, Nat. Prod. Rep. 1994, 11, 555-576;
35. k) K. W. Bentley, Nat. Prod. Rep. 1995, 12, 419-441;
36. l) M. Williams, J. Robinson, J. Neurosci. 1984, 4, 2906-2911;
37. m) M. W. Decker, D. J. Anderson, J. D. Brioni, D. L. Donnelly, C. H. Roberts, A. B. Kang, M. O'Neill, S. Piattoni-Kaplan, Swanson, J. P. Sullivan, Eur. J. Pharmacol. 1995, 280, 79-89.
38. a) L. F. Tietze, P. L. Steck, Eur. J. Org. Chem. 2001, 22, 4353-4356;
39. b) A. Basha, S. M. Weinreb, Tetrahedron Lett. 1977, 1465-1468.
40. G. Stork, A. Brizzolara, H. Landesman, J. Szmuszkovicz, R. J. Terrell, J. Am. Chem. Soc. 1963, 85, 207-222.
41. 4, and the solvent was removed in vacuum. The crude product was purified by column chromatography on silica (petroleum ether/ ethyl acetate = 1:1).
42. 3, TMS): δ = 174.9 (C-6), 147.6 (C-12), 147.1 (C-11), 134.7 (C-13a), 125.6 (C-9a), 111.7 (C-10), 108.0 (C-13), 62.09 (C-13b), 55.99 (OMe at C-11), 55.67 (OMe at C-12), 37.51 (C4a), 36.46 (C-8), 35.74 (C-5), 34.67 (C-4), 27.02 (C-1, C-9), 20.63 (C-2), 20.20 ppm (C-3).
43. 3, TMS): δ = 172.16 (C-7), 147.4 (C-12), 146.9 (C-13), 135.4 (C-14a), 126.84 (C-10a), 112.2 (C-14), 105.9 (C-11), 61.27 (C-14b), 55.96 (OMe at C-12), 55.43 (OMe at C-13), 40.47 (C-6), 35.75 (C-4a), 34.91 (C-9), 28.38 (C-5), 26.62 (C-10), 25.77 (C-4), 25.56 (C-1), 22.19 (C-2), 21.35 ppm (C-3).