Stereoselective synthesis of nitrogen-containing heterocycles via nickel-catalyzed cyclization of 1,3-diene and aldehyde: Formal total synthesis of (-)-elaeokanine C

Tetrahedron

Volumn 54, Issue 7, 1998, Pages 1153-1168

  Sato, Yoshihiro ^a   Saito, Nozomi ^a   Mori, Miwako ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKADIENE; ALKALOID; HETEROCYCLIC COMPOUND; INDOLIZIDINE DERIVATIVE; NICKEL; PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CYCLIZATION; DRUG SYNTHESIS; PRIORITY JOURNAL; STEREOSPECIFICITY;

EID: 0032510184     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10215-0     Document Type: Article

References (35)

1. 1. Reed, H. W. B. J. Chem. Soc. 1954, 1931.
2. 2. For reviews, see: (a) Jolly, P. W. In Comprehensive Organometallic Chemistry; Wilkinson, G.; Stone, F. G. A.; Abel, E. W., Eds.; Pergamon: New York, 1982; Vol. 8, p 613.
3. (b) Keim, W.; Behr, A.; Roper, M. ibid. p 371.
4. (c) Fischer, K.; Jonas, K.; Misbach, P.; Stabba, R.; Wilke, G. Angew Chem., Int. Ed. Engl. 1973, 12, 943.
5. (d) Heimback, P. ibid. 1973, 12, 975.
6. (e) Wilke, G. ibid. 1988, 27, 185.
7. 3. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089 and references cited therein.
8. 4. Wender, P. A.; Smith, T. E. J. Org. Chem. 1995, 60, 2962 and refereneces cited therein.
9. 5. (a) Tamao, K.; Kobayashi, K.; Ito, Y. Syn. Lett. 1992, 539.
10. (b) Tamao, K.; Kobayashi, K.; Ito, Y. J. Synth. Org. Chem. Jpn. 1990, 48, 381.
11. 6. (a) Sato, Y.; Takimoto, M.; Hayashi, K.; Katsuhara, T.; Takagi, K.; Mori, M. J. Am. Chem. Soc. 1994, 116, 9771.
12. (b) Sato, Y.; Takimoto, M.; Mori, M. Tetrahedron Lett. 1996, 37, 887.
13. (c) Sato, Y.; Takimoto, M.; Mori, M. Synlett 1997, 734.
14. 7. Preliminary communication for the construction of pyrrolizidine and indolizidine skeletons; Sato, Y.; Saito, N.; Mori, M. Tetrahedron Lett. 1997, 38, 3931.
15. 8. Mori, K. Tetrahedron 1974, 30, 3807.
16. 9. Mitsunobu, O. Synthesis 1980, 1.
17. 10. Howden, M. E. H.; Maercker, A.; Burdon, J.; Roberts, J. D. J. Am. Chem. Soc. 1966, 88, 1732.
18. 11. (a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
19. (b) Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
20. 4 gave the alcohol 32, again with over 99% ee, which indicates that no epimerization occurred during conversion of 32 into 33.
21. 13. Saijo, S.; Wada, M.; Himizu, J-i.; Ishida, A. Chem. Pharm. Bull. 1980, 28, 1449.
22. 14. For isolation of (-)-Elaeokanine C; (a) Hart, N. K.; Johns, S. R.; Lamberton, J. A. Chem. Commun. 1971, 460.
23. (b) Hart, N. K.; Johns, S. R.; Lamberton, J. A. Aust. J. Chem. 1972, 25, 817.
24. 15. For racemic syntheses of Elaeokanine C; (a) Tufariello, J. J.; Ali, S. A. Tetrahedron Lett. 1979, 4445.
25. (b) Howard, A. S.; Gerrans, G. C.; Meerholz, C. A. Tetrahedron Lett. 1980, 27, 1373.
26. (c) Watanabe, T.; Nakashita, Y.; Katayama, S; Yamauchi, M. Heterocycles 1980, 14, 1433.
27. (d) Otomasu, H.; Takatsu, N.; Honda, T.; Kametani, T. Heterocycles 1982, 19, 511.
28. (e) Otomasu, H.; Takatsu, N.; Honda, T.; Kametani, T. Tetrahedron 1982, 38, 2627.
29. (f) Shono, T.; Matsumura, Y.; Uchida, K.; Tsubata, K.; Makino, A. J. Org. Chem. 1984, 49, 300.
30. (g) Takahata, H.; Yamabe, K.; Suzuki, T.; Yamazaki, T. Heterocycles 1986, 24, 37.
31. (h) Gribble, G. W.; Switzer, F. L.; Soll, R. M. J. Org. Chem. 1988, 53, 3164.
32. Also see ref 8 (b). For the syntheses of (+)-Elaeokanine C; (i) Comins, D. L.; Hong, H. J. Am. Chem. Soc. 1991, 113, 6672.
33. (j) Arai, Y.; Kontani, T.; Koizumi, T. Tetrahedron: Asymmetry 1992, 3, 535.
34. (k) Arai, Y.; Kontani, T.; Koizumi, T. J. Chem. Soc., Perkin Trans. I 1994, 15.
35. 16. Kraus, G. A; Frazier, K. J. Org. Chem. 1980, 45, 2579.