Multicomponent linchpin coupling of silyl dithianes employing an N-Ts aziridine as the second electrophile: Synthesis of (-)-indolizidine 223AB

Organic Letters

Volumn 6, Issue 9, 2004, Pages 1493-1495

  Smith III, Amos B ^a   Kim, Dae Shik ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE; INDOLIZIDINE 223AB; INDOLIZIDINE ALKALOID; SILYL DITHIANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; SYNTHESIS;

AZIRIDINES; INDOLIZINES; MOLECULAR CONFORMATION; QUINOLIZINES; STEREOISOMERISM; SULFUR COMPOUNDS;

EID: 2442587600     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049601b     Document Type: Article

References (54)

1. (a) Corey, E. J.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1965, 4, 1075.
2. (b) Seebach, D.; Corey, E. J. J. Org. Chem. 1975, 40, 231.
3. Reviews: (a) Seebach, D. Synthesis 1969, 1, 17. (b) Grobel, B. T.; Seebach, D. Synthesis 1977, 357. (c) Page, P. C. B.; Van Niel, M. B.; Prodger, J. C. Tetrahedron 1989, 45, 7643. (d) Kolb, M. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley & Sons: Chichester, 1995; Vol. 5, p 2983. (e) Yus, M.; Najera, C.; Foubelo, F. Tetrahedron 2003, 59, 6147.
4. Reviews: (a) Seebach, D. Synthesis 1969, 1, 17. (b) Grobel, B. T.; Seebach, D. Synthesis 1977, 357. (c) Page, P. C. B.; Van Niel, M. B.; Prodger, J. C. Tetrahedron 1989, 45, 7643. (d) Kolb, M. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley & Sons: Chichester, 1995; Vol. 5, p 2983. (e) Yus, M.; Najera, C.; Foubelo, F. Tetrahedron 2003, 59, 6147.
5. Reviews: (a) Seebach, D. Synthesis 1969, 1, 17. (b) Grobel, B. T.; Seebach, D. Synthesis 1977, 357. (c) Page, P. C. B.; Van Niel, M. B.; Prodger, J. C. Tetrahedron 1989, 45, 7643. (d) Kolb, M. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley & Sons: Chichester, 1995; Vol. 5, p 2983. (e) Yus, M.; Najera, C.; Foubelo, F. Tetrahedron 2003, 59, 6147.
6. Reviews: (a) Seebach, D. Synthesis 1969, 1, 17. (b) Grobel, B. T.; Seebach, D. Synthesis 1977, 357. (c) Page, P. C. B.; Van Niel, M. B.; Prodger, J. C. Tetrahedron 1989, 45, 7643. (d) Kolb, M. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley & Sons: Chichester, 1995; Vol. 5, p 2983. (e) Yus, M.; Najera, C.; Foubelo, F. Tetrahedron 2003, 59, 6147.
7. Reviews: (a) Seebach, D. Synthesis 1969, 1, 17. (b) Grobel, B. T.; Seebach, D. Synthesis 1977, 357. (c) Page, P. C. B.; Van Niel, M. B.; Prodger, J. C. Tetrahedron 1989, 45, 7643. (d) Kolb, M. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley & Sons: Chichester, 1995; Vol. 5, p 2983. (e) Yus, M.; Najera, C.; Foubelo, F. Tetrahedron 2003, 59, 6147.
8. (a) Smith, A. B., III; Condon, S. M.; McCauley, J. A. Acc. Chem. Res. 1998, 31, 35 and references therein,
9. (b) Smith, A. B., III; Lodise, S. A. Org. Lett. 1999, 1, 1249.
10. (c) Smith, A. B., III; Doughty, V. A.; Lin, Q.; Zhuang, L.; McBriar, M. D.; Boldi, A. M.; Moser, W. H.; Murase, N.; Nakayama, K.; Sobukawa, M. Angew. Chem., Int. Ed. 2001, 40, 191.
11. (d) Smith, A. B., III; Lin, Q.; Doughty, V. A.; Zhuang, L.; McBriar, M. D.; Kerns, J. K.; Brook, C. S.; Murase, N.; Nakayama, K. Angew. Chem., Int. Ed. 2001, 40, 196.
12. (e) Smith, A. B., III; Adams, C. M.; Lodise Barbosa, S. A.; Degnan, A. P. J. Am. Chem. Soc. 2003, 125, 350.
13. (f) Smith, A. B., III; Zhu, W.; Shirakami, S.; Sfouggatakis, C.; Doughty, V. A.; Bennett, C. S.; Sakamoto, Y. Org. Lett. 2003, 5, 761.
14. (a) Smith, A. B., III; Boldi, A. M. J. Am. Chem. Soc. 1997, 119, 6925.
15. Also see: (b) Smith, A. B., III; Pitram, S. M.; Boldi, A. M.; Gaunt, M. J.; Sfouggatakis, C.; Moser, W. H. J. Am. Chem. Soc. 2003, 125, 14435.
16. (a) Smith, A. B., III; Zhuang, L.; Brook, C. S.; Boldi, A. M.; McBriar, M. D.; Moser, W. H.; Murase, N.; Nakayama, K.; Verhoest, P. R.; Lin, Q. Tetrahedron Lett. 1997, 38, 8667.
17. (b) Smith, A. B., III; Zhuang, L.; Brook, C. S.; Lin, Q.; Moser, W. H.; Trout, R. E. L.; Boldi, A. M. Tetrahedron Lett. 1997, 38, 8671.
18. (c) Smith, A. B., III; Lin, Q.; Nakayama, K.; Boldi, A. M.; Brook, C. S.; McBriar, M. D.; Moser, W. H.; Sobukawa, M.; Zhuang, L. Tetrahedron Lett. 1997, 38, 8675.
19. (d) Smith, A. B., III; Pitram, S. M. Org. Lett. 1999, 1, 2001.
20. (e) Smith, A. B., III; Doughty V. A.; Sfouggatakis, C.; Bennett, C. S.; Koyanagi J.; Takeuchi, M. Org. Lett. 2002, 4, 783.
21. (f) Smith, A. B., III; Pitram, S. M.; Fuertes, M. J. Org. Lett. 2003, 5, 2751.
22. (g) Smith, A. B., III; Pitram, S. M.; Boldi, A. M.; Gaunt, M. J.; Sfouggatakis, C.; Moser, W. H. J. Am. Chem. Soc. 2003, 125, 14435.
23. For N-Ts aziridine ring-opening reactions of lithiated dithiane anions, see: (a) Bates, G. S. J. Chem. Soc., Chem. Commun. 1979, 161. (b) Howson, W.; Osborn, H. M. I.; Sweeney, J. J. Chem. Soc., Perkin Trans, 1 1995, 2439. (c) Mao, H.; Joly, G. J.; Peeters, K.; Hoornaert, G. J.; Compernolle, F. Tetrahedron 2001, 57, 6955. (d) Reich, H. J.; Sanders, A. W.; Fiedler, A. T.; Bevan, M. J. J. Am. Chem. Soc. 2002, 124, 13386.
24. For N-Ts aziridine ring-opening reactions of lithiated dithiane anions, see: (a) Bates, G. S. J. Chem. Soc., Chem. Commun. 1979, 161. (b) Howson, W.; Osborn, H. M. I.; Sweeney, J. J. Chem. Soc., Perkin Trans, 1 1995, 2439. (c) Mao, H.; Joly, G. J.; Peeters, K.; Hoornaert, G. J.; Compernolle, F. Tetrahedron 2001, 57, 6955. (d) Reich, H. J.; Sanders, A. W.; Fiedler, A. T.; Bevan, M. J. J. Am. Chem. Soc. 2002, 124, 13386.
25. For N-Ts aziridine ring-opening reactions of lithiated dithiane anions, see: (a) Bates, G. S. J. Chem. Soc., Chem. Commun. 1979, 161. (b) Howson, W.; Osborn, H. M. I.; Sweeney, J. J. Chem. Soc., Perkin Trans, 1 1995, 2439. (c) Mao, H.; Joly, G. J.; Peeters, K.; Hoornaert, G. J.; Compernolle, F. Tetrahedron 2001, 57, 6955. (d) Reich, H. J.; Sanders, A. W.; Fiedler, A. T.; Bevan, M. J. J. Am. Chem. Soc. 2002, 124, 13386.
26. For N-Ts aziridine ring-opening reactions of lithiated dithiane anions, see: (a) Bates, G. S. J. Chem. Soc., Chem. Commun. 1979, 161. (b) Howson, W.; Osborn, H. M. I.; Sweeney, J. J. Chem. Soc., Perkin Trans, 1 1995, 2439. (c) Mao, H.; Joly, G. J.; Peeters, K.; Hoornaert, G. J.; Compernolle, F. Tetrahedron 2001, 57, 6955. (d) Reich, H. J.; Sanders, A. W.; Fiedler, A. T.; Bevan, M. J. J. Am. Chem. Soc. 2002, 124, 13386.
27. There is one report of an intramolecular linchpin reaction between a dithiane and the 1,4-biselectrophile, 1,2-epimino-3,4-epoxy-(N-Ts)butane. in which the aziridine moiety played a role as the second electrophile: Harms, G.; Schaumann, E.; Adiwidjaja, G. Synthesis 2001, 4, 577.
28. (a) Daly, J. W.; Brown, G. B.; Mensah-Dwumah, M. M.; Meyers, C. W. Toxicon 1978, 16, 163.
29. (b) Tokuyama, T.; Nishimori, N.; Karle, I. K.; Edwards, M. W.; Daly, J. W. Tetrahedron 1986, 42, 3453.
30. For synthesis of (-)-indolizidine 223AB, see: (c) Royer, J.; Husson, H. P. Tetrahedron Lett. 1985, 26, 1515.
31. (d) Taber, D. F.; Deker, P. B.; Silverberg, L. J. J. Org. Chem. 1992, 57, 5990.
32. (e) Machinaga, N.; Kibayashi, C. J. Org. Chem. 1992, 57, 5178.
33. (f) Fleurant, A.; Célérier, J. P.; Lhommet, G. Tetrahedron: Asymmetry 1993, 4, 1429.
34. (g) Muraoka, O.; Okumura, K.; Maeda, T.; Tanabe, G.; Momose, T. Tetrahedron: Asymmetry 1994, 5, 317.
35. (h) Pilli, R. A.; Dias, L. C.; Maldaner, A. O. J. Org. Chem. 1995, 60, 717.
36. Takahat, H.; Bandoh, H.; Momose, T. Heterocycles 1995, 41, 1797.
37. (j) Momose, T.; Toshima, M.; Koike, Y.; Toyooka, N.; Hirai, Y. J. Chem. Soc., Perkin Trans. 1 1997, 9, 1315.
38. (k) Célimène, C.; Dhimane, H.; Lhommet, G. Tetrahedron 1998, 54, 10457.
39. Lee, E.; Jeong, E. J.; Min, S. J.; Hong, S.; Lim, J.; Kim, S. K.; Kim, H. J.; Choi, B. G.; Koo, K. C. Org. Lett. 2000, 2, 2169.
40. (a) Oppolzer, W.; Flaskamp, E.; Bieber, L. W. Helv. Chim. Acta 2001, 84, 141.
41. (b) Oka, T.; Yasusa, T.; Ando, T.; Watanabe, M.; Yoneda, F.; Ishida, T.; Knoll, J. Bioorg. Med. Chem. 2001, 9, 1213.
42. (a) Frantz, D. E.; Fässler, R.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 1806.
43. (b) Anand, N. K.; Carreira, E. M. J. Am. Chem. Soc. 2001, 123, 9687.
44. (a) Annis, D. A.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 4147.
45. (b) Furrow, M. E.; Schaus, S. E.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 6776.
46. (c) Schaus, S. E.; Brandes, B. D.; Larrow, J. F.; Tokunaga, M.; Hansen, K. B.; Gould, A. E.; Furrow, M. E.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 1307.
47. Absolute configuration was established by Kakisawa analysis of the Mosher esters of (-)-8: Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.
48. (a) Jiang, B.; Chen, Z.; Xiong, W. Chem. Commun. 2002, 1524.
49. Using (+)-N-methyl ephedrine as a chiral ligand, we obtained (-)-8 in 44 % isolated yield and 96 % ee. For preparation of (-)-7, see: (b) Jiang, B.; Chen, Z.; Tang, X. Org. Lett. 2002, 4, 3451.
50. 12 of the Mosher esters of diol 11.
51. Chang, J.; Paquette, L. A. Org. Lett. 2002, 4, 253.
52. In step C, rapid warming to 0°C after addition of aziridine (-)-5 proved to be more consistent and furnished better yields. Slow warming over 1-2 h resulted in capricious behavior (ca. 30-50%), in conjunction with large amounts of (-)-12.
53. Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224. Without the dithiane moiety, the first cyclization was very slow (40 h), resulting in low yield (55% for mesylation and the first cyclization).
54. 8h -88° (c 0.50. MeOH)).