Application of a stereospecific intramolecular allenylsilane imino ene reaction to enantioselective total synthesis of the 5,11- methanomorphanthridine class of Amaryllidaceae alkaloids

Journal of the American Chemical Society

Volumn 119, Issue 25, 1997, Pages 5773-5784

  Jin, Jian ^a   Weinreb, Steven M ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; MORPHANTHRIDINE DERIVATIVE; NATURAL PRODUCT; SILANE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; ENANTIOMER; MOLECULAR INTERACTION; STEREOSPECIFICITY; SYNTHESIS;

EID: 0030741435     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja970839n     Document Type: Article

References (28)

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2. For recent reviews, see: (a) Martin, S. F. The Amaryllidaceae Alkaloids. In The Alkaloids; Brossi, A., Ed.; Academic Press: San Diego, 1987; Vol. 30, p 252. (b) Lewis, J. R. Nat. Prod. Rep. 1993, 10, 291.
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22. (e) Weinreb, S. M.; Smith, D. T.; Jin, J. Synthesis, in press. For a review of imino ene reactions, see: Borzilleri, R. M.; Weinreb, S. M. Synthesis 1995, 347.
23. (e) Weinreb, S. M.; Smith, D. T.; Jin, J. Synthesis, in press. For a review of imino ene reactions, see: Borzilleri, R. M.; Weinreb, S. M. Synthesis 1995, 347.
24. For intermolecular reactions of allenylsilanes with electrophiles via a non-pericyclic process, see: (a) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925. (b) Danheiser, R. L.; Carini, D. J.; Kwasigroch, C. A. J. Org. Chem. 1986,51, 3870. (c) Danheiser, R. L.; Kwasigroch, C. A.; Tsai, Y.-M. J. Am. Chem. Soc. 1985, 107, 7233. (d) Danheiser, R. L.; Stoner, E. J.; Koyama, H.; Yamashita, D. S.; Klade, C. A. J. Am. Chem. Soc. 1989, 111, 4407. (e) Becker, D. A.; Danheiser, R. L. J. Am. Chem. Soc. 1989, 111, 389.
25. For intermolecular reactions of allenylsilanes with electrophiles via a non-pericyclic process, see: (a) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925. (b) Danheiser, R. L.; Carini, D. J.; Kwasigroch, C. A. J. Org. Chem. 1986,51, 3870. (c) Danheiser, R. L.; Kwasigroch, C. A.; Tsai, Y.-M. J. Am. Chem. Soc. 1985, 107, 7233. (d) Danheiser, R. L.; Stoner, E. J.; Koyama, H.; Yamashita, D. S.; Klade, C. A. J. Am. Chem. Soc. 1989, 111, 4407. (e) Becker, D. A.; Danheiser, R. L. J. Am. Chem. Soc. 1989, 111, 389.
26. For intermolecular reactions of allenylsilanes with electrophiles via a non-pericyclic process, see: (a) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925. (b) Danheiser, R. L.; Carini, D. J.; Kwasigroch, C. A. J. Org. Chem. 1986,51, 3870. (c) Danheiser, R. L.; Kwasigroch, C. A.; Tsai, Y.-M. J. Am. Chem. Soc. 1985, 107, 7233. (d) Danheiser, R. L.; Stoner, E. J.; Koyama, H.; Yamashita, D. S.; Klade, C. A. J. Am. Chem. Soc. 1989, 111, 4407. (e) Becker, D. A.; Danheiser, R. L. J. Am. Chem. Soc. 1989, 111, 389.
27. For intermolecular reactions of allenylsilanes with electrophiles via a non-pericyclic process, see: (a) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925. (b) Danheiser, R. L.; Carini, D. J.; Kwasigroch, C. A. J. Org. Chem. 1986,51, 3870. (c) Danheiser, R. L.; Kwasigroch, C. A.; Tsai, Y.-M. J. Am. Chem. Soc. 1985, 107, 7233. (d) Danheiser, R. L.; Stoner, E. J.; Koyama, H.; Yamashita, D. S.; Klade, C. A. J. Am. Chem. Soc. 1989, 111, 4407. (e) Becker, D. A.; Danheiser, R. L. J. Am. Chem. Soc. 1989, 111, 389.
28. For intermolecular reactions of allenylsilanes with electrophiles via a non-pericyclic process, see: (a) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925. (b) Danheiser, R. L.; Carini, D. J.; Kwasigroch, C. A. J. Org. Chem. 1986,51, 3870. (c) Danheiser, R. L.; Kwasigroch, C. A.; Tsai, Y.-M. J. Am. Chem. Soc. 1985, 107, 7233. (d) Danheiser, R. L.; Stoner, E. J.; Koyama, H.; Yamashita, D. S.; Klade, C. A. J. Am. Chem. Soc. 1989, 111, 4407. (e) Becker, D. A.; Danheiser, R. L. J. Am. Chem. Soc. 1989, 111, 389.