Intramolecular imino Diels-Alder reaction of a 3-vinyl indole: Application to a total synthesis of (±)-eburnamonine

Journal of Organic Chemistry

Volumn 64, Issue 20, 1999, Pages 7586-7593

  Grieco, Paul A ^a   Kaufman, Michael D ^b  

^a MONTANA STATE UNIVERSITY   (United States)

^b INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

IMINE; VINBURNINE;

ARTICLE; CATALYSIS; CHEMICAL BINDING; MOLECULAR INTERACTION; SYNTHESIS;

EID: 0033214865     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9909960     Document Type: Article

References (37)

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2. Larsen, S. D.; Grieco, P. A. J. Am. Chem. Soc. 1985, 107, 1768. Grieco, P. A.; Larsen, S. D.; Forbare, W. F. Tetrahedron Lett. 1986, 27, 1975. Grieco, P. A.; Larsen, S. D. J. Org. Chem. 1986, 51, 3553. Grieco, P. A.; Parker, D. T. J. Org. Chem. 1988, 53, 3, 3325. Grieco, P. A.; Parker, D. T. J. Org. Chem. 1988, 53, 3658. Also see: Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic & Professional: Glasgow, 1998.
3. Larsen, S. D.; Grieco, P. A. J. Am. Chem. Soc. 1985, 107, 1768. Grieco, P. A.; Larsen, S. D.; Forbare, W. F. Tetrahedron Lett. 1986, 27, 1975. Grieco, P. A.; Larsen, S. D. J. Org. Chem. 1986, 51, 3553. Grieco, P. A.; Parker, D. T. J. Org. Chem. 1988, 53, 3, 3325. Grieco, P. A.; Parker, D. T. J. Org. Chem. 1988, 53, 3658. Also see: Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic & Professional: Glasgow, 1998.
4. Larsen, S. D.; Grieco, P. A. J. Am. Chem. Soc. 1985, 107, 1768. Grieco, P. A.; Larsen, S. D.; Forbare, W. F. Tetrahedron Lett. 1986, 27, 1975. Grieco, P. A.; Larsen, S. D. J. Org. Chem. 1986, 51, 3553. Grieco, P. A.; Parker, D. T. J. Org. Chem. 1988, 53, 3, 3325. Grieco, P. A.; Parker, D. T. J. Org. Chem. 1988, 53, 3658. Also see: Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic & Professional: Glasgow, 1998.
5. Larsen, S. D.; Grieco, P. A. J. Am. Chem. Soc. 1985, 107, 1768. Grieco, P. A.; Larsen, S. D.; Forbare, W. F. Tetrahedron Lett. 1986, 27, 1975. Grieco, P. A.; Larsen, S. D. J. Org. Chem. 1986, 51, 3553. Grieco, P. A.; Parker, D. T. J. Org. Chem. 1988, 53, 3, 3325. Grieco, P. A.; Parker, D. T. J. Org. Chem. 1988, 53, 3658. Also see: Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic & Professional: Glasgow, 1998.
6. Larsen, S. D.; Grieco, P. A. J. Am. Chem. Soc. 1985, 107, 1768. Grieco, P. A.; Larsen, S. D.; Forbare, W. F. Tetrahedron Lett. 1986, 27, 1975. Grieco, P. A.; Larsen, S. D. J. Org. Chem. 1986, 51, 3553. Grieco, P. A.; Parker, D. T. J. Org. Chem. 1988, 53, 3, 3325. Grieco, P. A.; Parker, D. T. J. Org. Chem. 1988, 53, 3658. Also see: Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic & Professional: Glasgow, 1998.
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12. A survey of the literature found no reports of 3-vinylindoles undergoing [4 + 2] cycloaddition with imines. In contrast, there are numerous reports of 3-vinylindoles reacting with more traditional dienophiles: Eberle, M. K.; Shapiro, M. J.; Stucki, R J. Org. Chem. 1987, 4661. Simoji, Y.; Saito, F.; Tomita, K.; Morisawa, Y. Heterocycles 1991, 32, 2389.
13. A survey of the literature found no reports of 3-vinylindoles undergoing [4 + 2] cycloaddition with imines. In contrast, there are numerous reports of 3-vinylindoles reacting with more traditional dienophiles: Eberle, M. K.; Shapiro, M. J.; Stucki, R J. Org. Chem. 1987, 4661. Simoji, Y.; Saito, F.; Tomita, K.; Morisawa, Y. Heterocycles 1991, 32, 2389.
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28. To date there have been two additional reports of imino Diels-Alder reactions occurring in 5.0 M lithium perchlorate-diethyl ether solution; see: (a) Katagiri, N.; Kurimoto, A.; Kaneko, C. Chem. Pharm. Bull. 1992, 40, 1737. (b) Takemoto, Y.; Ueda, S.; Takeuchi, J.; Nakamoto, T.; Iwata, C. Tetrahedron Lett. 1994, 35, 8821.
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