Erratum: Catalytic Selective Cyclizations of Aminocyclopropanes: Formal Synthesis of Aspidospermidine and Total Synthesis of Goniomitine (Angewandte Chemie - International Edition (2010) 49 (5767-5770) DOI 10.1002/anie.201001853);Catalytic selective cyclizations of aminocyclopropanes: Formal synthesis of aspidospermidine and total synthesis of goniomitine

Angewandte Chemie - International Edition

Volumn 49, Issue 33, 2010, Pages 5767-5770

  De Simone, Filippo ^a   Gertsch, Jürg ^b   Waser, Jérôme ^a  

^a EPFL   (Switzerland)

^b Institute of Biochemistry and Molecular Biology   (Switzerland)

Author keywords

Alkaloids; Antitumor agents; Cyclization; Heterocycles; Regioselectivity; alkaloids; antitumor agents; cyclization; heterocycles; regioselectivity

Indexed keywords

ALKALOIDS; CELL CULTURE; REGIOSELECTIVITY; SYNTHESIS (CHEMICAL);

ANTI-TUMOR AGENTS; CYCLIZATIONS; FORMAL SYNTHESIS; HETEROCYCLES; INDOLE RINGS; REACTION CONDITIONS; TOTAL SYNTHESIS; TUMOR CELL LINES;

CYCLIZATION;

EID: 77955329354     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201190034     Document Type: Erratum

References (53)

1. a) A. F. Pozharskii, A. R. Katritsky, A. T. Soldatenkov in Heterocycles in Life and Society: An Introduction to Heterocyclic Chemistry and Biochemistry and the Role of Heterocycles in Science Technology, Medicine and Agriculture, Wiley-VCH, Weinheim, 1997
2. b) J. Clardy, C. Walsh, Nature 2004, 432, 829.
3. S. M. Ma in Handbook of Cyclization Reactions, Wiley-VCH, Weinheim, 2009.
4. F. De Simone, J. Andres, R. Torosantucci, J. Waser, Org. Lett. 2009, 11, 1023.
5. a) I. N. Nazarov, I.I. Zaretskaya, Izv. Akad. Nauk SSSR Ser. Khim. 1941, 211; For reviews, see:
6. b) K. L. Habermas, S. E. Denmark, T. K. Jones, Org. React. 1994, 45, 1-158
7. c) A. J. Frontier, C. Collison, Tetrahedron 2005, 61, 7577
8. d) H. Pellissier, Tetrahedron 2005, 61, 6479
9. e) M. A. Tius, Eur. J. Org. Chem. 2005, 2193
10. f) W. Nakanishi, F. G. West, Curr. Opin. Drug Discovery Dev. 2009, 12, 732.
11. a) W. S. Murphy, S. Wattanasin, Tetrahedron Lett. 1980, 21, 1887
12. b) W. S. Murphy, S. Wattanasin, J. Chem. Soc. Perkin Trans. 1 1981, 2920
13. c) W. S. Murphy, S. Wattanasin, J. Chem. Soc. Perkin Trans. 1 1982, 1029
14. d) O. Tsuge, S. Kanemasa, T. Otsuka, T. Suzuki, Bull. Chem. Soc. Jpn. 1988, 61, 2897
15. e) V. K. Yadav, N. V. Kumar, Chem. Commun. 2008, 3774.
16. a) H. U. Reissig, R. Zimmer, Chem, Rev. 2003, 103, 1151
17. b) M. Yu, B. L. Pagenkopf, Tetrahedron 2005, 61, 321
18. c) F. De Simone, J. Waser, Synthesis 2009, 3353.
19. a) S. E. Malawista, H. Sato, K. G. Bensch, Science 1968, 160, 770
20. b) B. Gigant, C. G. Wang, R. B. G. Ravelli, F. Roussi, M. O. Steinmetz, P. A. Curmi, A. Sobel, M. Knossow, Nature 2005, 435, 519
21. c) F. Gueritte, J. Fahy, The Vinca Alkaloids, Anticancer Agents from Natural Products (Eds. : D. J. C. Newman, G. M. Kingston), Taylor & Francis, London, 2005.
22. For a few selected examples, see: a) G. Stork, J. E. Dolfini, J. Am. Chem. Soc. 1963, 85, 2872
23. b) J. P. Kutney, N. Abdurahm, P. Lequesne, E. Piers, I. Vlattas, J. Am. Chem. Soc. 1966, 88, 3656
24. c) T. Gallagher, P. Magnus, J. C. Huffman, J. Am. Chem. Soc. 1982, 104, 1140
25. d) E. Wenkert, T. Hudlicky, J. Org. Chem. 1988, 53, 1953
26. e) R. Iyengar, K. Schildknegt, J. Aube, Org. Lett. 2000, 2, 1625
27. f) M. A. Toczko, C. H. Heathcock, J. Org. Chem. 2000, 65, 2642
28. g) S. A. Kozmin, T. Iwama, Y. Huang, V. H. Rawal, J. Am. Chem. Soc. 2002, 124, 4628
29. h) L. A. Sharp, S. Z. Zard, Org. Lett. 2006, 8, 831
30. i) C. Sabot, K. C. Guerard, S. Canesi, Chem. Commun. 2009, 2941.
31. Isolation: a) L. Randriambola, J. C. Quirion, C. Kanfan, H. P. Husson, Tetrahedron Lett. 1987, 28, 2123; Total syntheses:
32. b) S. Takano, T. Sato, K. Inomata, K. Ogasawara, J. Chem. Soc. Chem. Commun. 1991, 462
33. c) C. L. Morales, B. L. Pagenkopf, Org. Lett. 2008, 10, 157; Analogs studies:
34. d) C. Hashimoto, H. P. Husson, Tetrahedron Lett. 1988, 29, 4563
35. e) G, Lewin, C. Schaeffer, Nat. Prod. Lett. 1995, 7, 227
36. f) G. Lewin, C. Schaeffer, P. H. Lambert, J. Org. Chem. 1995, 60, 3282
37. g) G. Lewin, C. Schaeffer, R. Hocquemiller, E. Jacoby, S. Leonce, A. Pierre, G. Atassi, Heterocycles 2000, 53, 2353.
38. See the Supporting Information for the synthesis of 4.
39. The cis stereochemistry was determined by two-dimensional NMR experiments. See the Supporting Information for details.
40. P. A. Grieco, M. D. Kaufman, J. Org. Chem. 1999, 64, 7586.
41. R. Beumer, C. Bubert, C. Cabrele, O. Vielhauer, M. Pietzsch, O. Reiser, J. Org. Chem. 2000, 65, 8960.
42. 4-(4,6-Dimethoxy-l,3,5-triazin-2-yl)-JV-methylmorpholinium chloride.
43. [13]
44. A. R. Katritzky, K. Akutagawa, Tetrahedron Lett. 1985, 26, 5935.
45. The structure of deprotected 15a was definitively confirmed by X-ray diffraction studies on the corresponding hydrochloride salt; see the Supporting Information.
46. B. E. Maryanoff, H. C. Zhang, J. H. Cohen, I. J. Turchi, C. A. Maryanoff, Chem. Rev. 2004, 104, 1431.
47. a) A. Jackson, N. D. V, Wilson, A. J. Gaskell, J. A. Joule, J. Chem. Soc. C 1969, 2738
48. b) P. Forns, A. Diez, M. Rubiralta, J. Org. Chem. 1996, 61, 7882
49. c) M. Amat, M. Perez, N. Llor, C. Escolano, F. J. Luque, E. Molins, J. Bosch, J. Org. Chem. 2004, 69, 8681
50. S. Cutri, A. Diez, M. Bonin, L. Micouin, H. P. Husson, Org. Lett. 2005, 7, 1911.
51. See the Supporting Information.
52. 13C NMR spectra fitted perfectly with the reported values for synthetic goniomitine, but small differences were apparent when compared with natural goniomitine. A comparison of the spectra is provided in the Supporting Information.
53. See the Supporting Information for more details. See also: J. Gertsch, F. Feyen, A. Bützberger, B. Gerber, B. Pfeiffer, K. H. Altmann, ChemBioChem 2009, 10, 2513.