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Volumn 62, Issue 6, 1997, Pages 1668-1674

Tandem [4 + 2]/[3 + 2] cycloadditions of nitroalkenes. 13. The synthesis of (-)-detoxinine

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; DETOXININE; UNCLASSIFIED DRUG;

EID: 0030966034     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962306n     Document Type: Article
Times cited : (95)

References (73)
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    • Racemic synthesis: (a) Häusler, J. Liebigs Ann. Chem. 1983, 982. Natural (-) enantiomer syntheses: (b) Ohfune, Y.; Nishio, H. Tetrahedron Lett. 1984, 25, 4133. (c) Joullie, M. M.; Ewing, W. R.; Harris, B. D.; Bhat, K. L. Tetrahedron 1986, 42, 2421. Kogen, H.; Kadokawa, H.; Kurabayahi, M. J. Chem. Soc., Chem. Commun. 1990, 1240. Unnatural (+) enantiomer synthesis: (e) Mulzer, J.; Meier, A.; Buschmann, J.; Luger, P. J. Org. Chem. 1996, 61, 566. Additionally, there are two formal synthesis of natural (-)-detoxinine on record, (f) Joullie, M. M.; Ewing, W. R. Heterocycles 1988, 27, 2843. (g) Takahata, H.; Banba, Y.; Tajima, M.; Momse, T. J. Org. Chem. 1991, 56, 240.
    • (1983) Liebigs Ann. Chem. , pp. 982
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    • Racemic synthesis: (a) Häusler, J. Liebigs Ann. Chem. 1983, 982. Natural (-) enantiomer syntheses: (b) Ohfune, Y.; Nishio, H. Tetrahedron Lett. 1984, 25, 4133. (c) Joullie, M. M.; Ewing, W. R.; Harris, B. D.; Bhat, K. L. Tetrahedron 1986, 42, 2421. Kogen, H.; Kadokawa, H.; Kurabayahi, M. J. Chem. Soc., Chem. Commun. 1990, 1240. Unnatural (+) enantiomer synthesis: (e) Mulzer, J.; Meier, A.; Buschmann, J.; Luger, P. J. Org. Chem. 1996, 61, 566. Additionally, there are two formal synthesis of natural (-)-detoxinine on record, (f) Joullie, M. M.; Ewing, W. R. Heterocycles 1988, 27, 2843. (g) Takahata, H.; Banba, Y.; Tajima, M.; Momse, T. J. Org. Chem. 1991, 56, 240.
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    • Ohfune, Y.1    Nishio, H.2
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    • Racemic synthesis: (a) Häusler, J. Liebigs Ann. Chem. 1983, 982. Natural (-) enantiomer syntheses: (b) Ohfune, Y.; Nishio, H. Tetrahedron Lett. 1984, 25, 4133. (c) Joullie, M. M.; Ewing, W. R.; Harris, B. D.; Bhat, K. L. Tetrahedron 1986, 42, 2421. Kogen, H.; Kadokawa, H.; Kurabayahi, M. J. Chem. Soc., Chem. Commun. 1990, 1240. Unnatural (+) enantiomer synthesis: (e) Mulzer, J.; Meier, A.; Buschmann, J.; Luger, P. J. Org. Chem. 1996, 61, 566. Additionally, there are two formal synthesis of natural (-)-detoxinine on record, (f) Joullie, M. M.; Ewing, W. R. Heterocycles 1988, 27, 2843. (g) Takahata, H.; Banba, Y.; Tajima, M.; Momse, T. J. Org. Chem. 1991, 56, 240.
    • (1986) Tetrahedron , vol.42 , pp. 2421
    • Joullie, M.M.1    Ewing, W.R.2    Harris, B.D.3    Bhat, K.L.4
  • 9
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    • Racemic synthesis: (a) Häusler, J. Liebigs Ann. Chem. 1983, 982. Natural (-) enantiomer syntheses: (b) Ohfune, Y.; Nishio, H. Tetrahedron Lett. 1984, 25, 4133. (c) Joullie, M. M.; Ewing, W. R.; Harris, B. D.; Bhat, K. L. Tetrahedron 1986, 42, 2421. Kogen, H.; Kadokawa, H.; Kurabayahi, M. J. Chem. Soc., Chem. Commun. 1990, 1240. Unnatural (+) enantiomer synthesis: (e) Mulzer, J.; Meier, A.; Buschmann, J.; Luger, P. J. Org. Chem. 1996, 61, 566. Additionally, there are two formal synthesis of natural (-)-detoxinine on record, (f) Joullie, M. M.; Ewing, W. R. Heterocycles 1988, 27, 2843. (g) Takahata, H.; Banba, Y.; Tajima, M.; Momse, T. J. Org. Chem. 1991, 56, 240.
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    • Additionally, there are two formal synthesis of natural (-)-detoxinine on record
    • Racemic synthesis: (a) Häusler, J. Liebigs Ann. Chem. 1983, 982. Natural (-) enantiomer syntheses: (b) Ohfune, Y.; Nishio, H. Tetrahedron Lett. 1984, 25, 4133. (c) Joullie, M. M.; Ewing, W. R.; Harris, B. D.; Bhat, K. L. Tetrahedron 1986, 42, 2421. Kogen, H.; Kadokawa, H.; Kurabayahi, M. J. Chem. Soc., Chem. Commun. 1990, 1240. Unnatural (+) enantiomer synthesis: (e) Mulzer, J.; Meier, A.; Buschmann, J.; Luger, P. J. Org. Chem. 1996, 61, 566. Additionally, there are two formal synthesis of natural (-)-detoxinine on record, (f) Joullie, M. M.; Ewing, W. R. Heterocycles 1988, 27, 2843. (g) Takahata, H.; Banba, Y.; Tajima, M.; Momse, T. J. Org. Chem. 1991, 56, 240.
    • (1996) J. Org. Chem. , vol.61 , pp. 566
    • Mulzer, J.1    Meier, A.2    Buschmann, J.3    Luger, P.4
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    • Racemic synthesis: (a) Häusler, J. Liebigs Ann. Chem. 1983, 982. Natural (-) enantiomer syntheses: (b) Ohfune, Y.; Nishio, H. Tetrahedron Lett. 1984, 25, 4133. (c) Joullie, M. M.; Ewing, W. R.; Harris, B. D.; Bhat, K. L. Tetrahedron 1986, 42, 2421. Kogen, H.; Kadokawa, H.; Kurabayahi, M. J. Chem. Soc., Chem. Commun. 1990, 1240. Unnatural (+) enantiomer synthesis: (e) Mulzer, J.; Meier, A.; Buschmann, J.; Luger, P. J. Org. Chem. 1996, 61, 566. Additionally, there are two formal synthesis of natural (-)-detoxinine on record, (f) Joullie, M. M.; Ewing, W. R. Heterocycles 1988, 27, 2843. (g) Takahata, H.; Banba, Y.; Tajima, M.; Momse, T. J. Org. Chem. 1991, 56, 240.
    • (1988) Heterocycles , vol.27 , pp. 2843
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    • Racemic synthesis: (a) Häusler, J. Liebigs Ann. Chem. 1983, 982. Natural (-) enantiomer syntheses: (b) Ohfune, Y.; Nishio, H. Tetrahedron Lett. 1984, 25, 4133. (c) Joullie, M. M.; Ewing, W. R.; Harris, B. D.; Bhat, K. L. Tetrahedron 1986, 42, 2421. Kogen, H.; Kadokawa, H.; Kurabayahi, M. J. Chem. Soc., Chem. Commun. 1990, 1240. Unnatural (+) enantiomer synthesis: (e) Mulzer, J.; Meier, A.; Buschmann, J.; Luger, P. J. Org. Chem. 1996, 61, 566. Additionally, there are two formal synthesis of natural (-)-detoxinine on record, (f) Joullie, M. M.; Ewing, W. R. Heterocycles 1988, 27, 2843. (g) Takahata, H.; Banba, Y.; Tajima, M.; Momse, T. J. Org. Chem. 1991, 56, 240.
    • (1991) J. Org. Chem. , vol.56 , pp. 240
    • Takahata, H.1    Banba, Y.2    Tajima, M.3    Momse, T.4
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    • For a recent example of the use of the temporary silicon tether in [3 + 2]-dipolar cycloadditions of nitronates see: Righi, P.; Marotta, E.; Laduzzi, A.; Rossini, G. J. Am. Chem. Soc. 1996, 118, 9446.
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    • Righi, P.1    Marotta, E.2    Laduzzi, A.3    Rossini, G.4
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    • Stone, F. G. A., West R., Eds.; Academic Press: New York, Chapter 1
    • For a review of silyl anions see: Tamao, K.; Kawachi, A. In Advances in Organometallic Chemistry; Stone, F. G. A., West R., Eds.; Academic Press: New York, 1995; Vol. 38, Chapter 1, p 1.
    • (1995) Advances in Organometallic Chemistry , vol.38 , pp. 1
    • Tamao, K.1    Kawachi, A.2
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    • note
    • Higher order silylcyanocuprates provided the β-silyl unsaturated ester in low yield. Additionally, multiple addition products were suspected as byproducts. Investigations with alternative copper source also failed.
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    • Ph. D. Thesis, University of Illinois
    • A similar observation was documented for nitroalkene bearing a 2 methylene tether with MAPh and bornanediol derived chiral vinyl ether. M. E. Schnute, Ph. D. Thesis, University of Illinois, 1995.
    • (1995)
    • Schnute, M.E.1
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    • Recovered (-)-26 from all hydrogenolysis reactions was determined to be of >99% ee by chiral HPLC (R,R-Whelk-O1, Regis)
    • Recovered (-)-26 from all hydrogenolysis reactions was determined to be of >99% ee by chiral HPLC (R,R-Whelk-O1, Regis).
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    • (b) For a useful protocol for the oxidation of hindered silanes, see Smitrovich, J. H.; Woerpel, K. A. J. Org. Chem. 1996, 61, 6044.
    • (1996) J. Org. Chem. , vol.61 , pp. 6044
    • Smitrovich, J.H.1    Woerpel, K.A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.