Synthesis of (±)-strychnofoline via a highly convergent selective annulation reaction

Chemistry - A European Journal

Volumn 12, Issue 32, 2006, Pages 8208-8219

  Lerchner, Andreas ^a   Carreira, Erick M ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

Alkaloids; Cyclopropanes; Spirocycles; Total synthesis

Indexed keywords

CYCLIC VOLTAMMETRY; ISOMERS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

ALKALOIDS; CYCLOPROPANES; SPIROCYCLES; TOTAL SYNTHESIS;

AMINES;

ANTINEOPLASTIC AGENT; INDOLE ALKALOID; INDOLIZINE DERIVATIVE; SPIRO COMPOUND; STRYCHNOFOLINE;

ARTICLE; CHEMICAL MODEL; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; CYCLIZATION; INDOLE ALKALOIDS; INDOLIZINES; MODELS, CHEMICAL; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 33751040813     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200600957     Document Type: Conference Paper

References (51)

1. L. Angenot, Plant. Med. Phytother. 1978, 2, 123.
2. L. Angenot, C. Coune, M. Tits, J. Pharm. Belg. 1978, 33, 11.
3. R. Bassleer, M. Depauw-Gillet, B. Massart, J. Marnette, P. Wiliquet, M. Caprasse, L. Angenot, Planta Med. 1982, 45, 123.
4. C. B. Cui, H. Kakeya, H. Osada, J. Antibiot. 1996, 49, 832.
5. J. C. Seaton, L. Marion, Can. J. Chem. 1957, 35, 1102.
6. M. Shamma, R. J. Shine, I. Kompis, T. Sticzay, F. Morsingh, J. Poisson, J. L. Pousset, J. Am. Chem. Soc. 1967, 89, 1739.
7. J.-C. Braekmann, M. Tirions-Lampe, J. Pecher, J. Bull. Soc. Chim. Belg. 1969, 78, 523.
8. A. Jossang, P. Jossang, H. A. Hadi, T. Sevenet, B. Bodo, J. Org. Chem. 1991, 56, 6527.
9. E. Wenkert, C.-J. Chang, A. O. Clouse, D. W. Cochran, J. Chem. Soc. Chem. Commun. 1970, 961.
10. R. B. Herbert, in "Heterocyclic Compounds", Vol. 25 (Ed.: J. E. Saxton), Wiley-Interscience, New York, 1983, Part 4, pp. 1-46.
11. a) A. R. Battersby, R. S. Kapil, J. A. Martin, L. Mo, J. Chem. Soc. Chem. Commun. 1968, 133;
12. b) S. Brechbühler-Bader, C. J. Coscia, P. Loew, D. Arigoni, J. Chem. Soc. Chem. Commun. 1968, 136;
13. c) P. Loew, D. Arigoni, J. Chem. Soc. Chem. Commun. 1968, 137.
14. A. R. Battersby, A. R. Burnett, P. G. Parsons, J. Chem. Soc. C 1969, 1187.
15. a) A. I. Scott, S.-L. Lee, J. Am. Chem. Soc. 1975, 97, 6906;
16. b) J. Stöckigt, H.-P. Husson, C. Kan-Fan, M. H. Zenk, J. Chem. Soc. Chem. Commun. 1977, 164.
17. A. R. Battersby, R. J. Parry, J. Chem. Soc. Chem. Commun. 1971, 30.
18. A number of synthetic strategies utilize such a rearrangement reaction for the synthesis of various oxindole alkaloids, see: a) J. Shavel, Jr., H. Zinnes, J. Am. Chem. Soc. 1962, 84, 1320;
19. b) N. Finch, W. I. Taylor, J. Am. Chem. Soc. 1962, 84, 1318;
20. c) E. Winterfeldt, A. J. Gaskell, K. Tilmann, J. Radunz, M. Walkowiak, Chem. Ber. 1969, 102, 3358.
21. a) J. B. Hendrickson, R. A. Silva, J. Am. Chem. Soc. 1962, 84, 643-650;
22. b) Y. Ban, T. Oishi, Chem. Pharm. Bull. 1963, 11, 451;
23. c) E. E. van Tamelen, J. P. Yardley, M. Miyano, W. B. Hirashaw, Jr., J. Am. Chem. Soc. 1969, 91, 7333;
24. d) R. T. Brown, C. L. Chapple, R. Platt, Tetrahedron Lett. 1976, 17, 1401;
25. e) P. Rosenmund, M. Hosseini-Merescht, C. Bub, Liebigs Ann. Chem. 1994, 151.
26. W. A. Carroll, P. A. Grieco, J. Am. Chem. Soc. 1993, 115, 1164.
27. a) C. Fischer, C. Meyers, E. M. Carreira, Helv. Chim. Acta 2000, 83, 1175;
28. b) A. Lerchner, E. M. Carreira, J. Am. Chem. Soc. 2002, 124, 14826;
29. c) C. Meyers, E. M. Carreira, Angew. Chem. 2003, 115, 718;
30. Angew. Chem. Int. Ed. 2003, 42, 694;
31. d) for additional studies expanding the scope of this approach, see: M. E. Scott, W. Han, M. Lautens, Org. Lett. 2004, 6, 3309.
32. B. P. Alper, C. Meyers, A. Lerchner, D. R. Siegel, E. M. Carreira, Angew. Chem. 1999, 111, 3379;
33. Angew. Chem. Int. Ed. 1999, 38, 3186.
34. T. H. Lowry, in "Mechanism and Theory in Organic Chemistry" (Ed.: E. Mac Elree), Harper International Edition, London, 1987, pp. 367.
35. C. Marti, Ph.D. Thesis, ETH Zürich, No 15001 2003.
36. C. Schöpf, F. Braun, A. Komzak, Chem. Ber. 1956, 89, 1821.
37. a) H. Bibas, R. Koch, J. Wentrup, J. Org. Chem. 1998, 63, 2619;
38. b) H. Bock, R. Dammel, Chem. Ber. 1987, 120, 1971.
39. G. R. Cook, L. G. Beholz, R. G. Stille, J. Org. Chem. 1994, 59, 3575.
40. T. W. Greene, P. G. M. Wuts, in "Protective Groups in Organic Synthesis" (Ed.: T. W. Greene, P. G. M. Wuts), Wiley, New York, 1999, pp. 550-653.
41. a) C. Herdeis, C. Kaschinski, R. Karla, Tetrahedron: Asymmetry 1996, 7, 867;
42. b) C. Herdeis, H. P. Hubmann, Tetrahedron: Asymmetry 1992, 3, 1213.
43. M. Taddei, S. C. Migam, A. Mann, C. Wermuth, Synth. Commun. 1989, 19, 3139.
44. M. Sakaitani, Y. Ohfune, J. Org. Chem. 1990, 55, 870.
45. R. K. Dieter, R. R. Sharma, J. Org. Chem. 1996, 67, 4180.
46. 6-Methoxyisatine was prepared according to literature procedure and crystallized from acetone, see: V. H. Pavlidis, P. J. Perry, Synth. Commun. 1994, 24, 533.
47. R. T. Brown, in "Heterocyclic Compounds", Vol. 25 (Ed.: J. E. Saxon), Wiley-Interscience, New York, 1983, Part 4, pp. 85.
48. CCDC-211064 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
49. R. T. Brown, R. Platt, J. Chem. Soc. Chem. Commun. 1976, 357.
50. E. D. Cox, L. K. Hamaker, J. Li, P. Yu, L. D. Czerwinski, D. W. Bennett, J. M. Cook, J. Org. Chem. 1997, 62, 44.
51. N-Methyltryptamine was prepared from tryptamine in analogy to a literature procedure by Xu and co-workers, see: Y. Xu, J. M. Schaus, C. Walker, J. Krushinski, N. Adham, J. M. Zgombick, S. X. Liang, D. T. Kohlman, J. E. Audin, J. Med. Chem. 1999, 42, 526.