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Volumn 110, Issue 1, 1988, Pages 289-291

Extremely Short Chiral Synthesis of Bicyclic Alkaloids Having a Nitrogen Atom Ring Juncture

Author keywords

[No Author keywords available]

Indexed keywords

LUPININE; PYRROLIDINE DERIVATIVE;

EID: 0023874591     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00209a047     Document Type: Article
Times cited : (79)

References (16)
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    • The Pyrrolizidine Alkaloids
    • North-Holland, Amsterdam (b) A review in Japanese entitled “Chemistry of Pyrrolizidine Alkaloids”: Furuya, T.; Hikichi, M. J. Synth. Org. Chem. Jpn. 1977, 35, 653
    • Bull, L. B.; Culvenor, C. C. J.; Dick, A. T. The Pyrrolizidine Alkaloids; North-Holland, Amsterdam, 1968. (b) A review in Japanese entitled “Chemistry of Pyrrolizidine Alkaloids”: Furuya, T.; Hikichi, M. J. Synth. Org. Chem. Jpn. 1977, 35, 653.
    • (1968)
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    • Apsimon, J., Ed.; John Wiley and Sons, Inc.: New York, 1977: p 439. (b) For recent review papers of pyrrolizidine alkaloids, see: Robins, D. J. Nat. Prod. Rep. 1986, 3, 297 and earlier references in this series. (c) For recent review papers of indolizidine and quinolizidine alkaloids, see: Grundon. M. F. Nat. Prod. Rep. 1985, 2, 235 and earlier references in this series.
    • Stevens, R. V. In The Total Synthesis of Natural Products Vol. 3; Apsimon, J., Ed.; John Wiley and Sons, Inc.: New York, 1977: p 439. (b) For recent review papers of pyrrolizidine alkaloids, see: Robins, D. J. Nat. Prod. Rep. 1986, 3, 297 and earlier references in this series. (c) For recent review papers of indolizidine and quinolizidine alkaloids, see: Grundon. M. F. Nat. Prod. Rep. 1985, 2, 235 and earlier references in this series.
    • The Total Synthesis of Natural Products , vol.3
    • Stevens, R.V.1
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    • Recent synthetic works on (±)-trachelanthamidine (b) Nossin, P. M. M.; Spechamp, W. N. Tetrahedron Lett. 1979, 4411. (c) Kraus, G. A.; Neuenschwander, K. J. Am. Chem. Soc. 1980, 21, 3841. (d) Terao, Y.; Imai, N.; Achiwa, K.; Sekiya, M. Chem. Pharm. Bull. 1982, 30, 3167. (e) Hart, D. J.; Yang, T.-K. Tetrahedron Lett. 1982, 23, 2761. (f) Blum, Z.; Ekstroem, M,; Wistrand, L. G. Acta Chem. Scand., Ser. B 1984, B38, 297. (g) Kametani, T.; Higashiyama, K.; Otomasu, H.; Honda, T. Heterocycles 1984, 22, 729. (h) Shono, T.; Matsumara, Y.; Uchida, K.; Tsubata, K.; Makino, A. J. Org. Chem. 1984, 49, 300. (i) Chamberlin, A. R.; Nguyen, H. D.; Chung, J. Y. L. J. Am. Chem. Soc. 1984, 49, 1682. (j) Hudlicky, T.; Frazier, J. O.; Seoane, G.; Tiedje. M.; Seoane, A.; Kwart, L. D.; Beal, C. J. Am. Chem. Soc. 1986, 108, 3755. (k) Kametani, T.; Yukawa, H.; Honda, T. J. Chem. Soc., Chem. Commun. 1986, 651
    • Recent synthetic works on (±)-trachelanthamidine: (a) Danishefsky, S.; McKee, R.; Singh, R. K. J. Am. Chem. Soc. 1977, 99, 4783, (b) Nossin, P. M. M.; Spechamp, W. N. Tetrahedron Lett. 1979, 4411. (c) Kraus, G. A.; Neuenschwander, K. J. Am. Chem. Soc. 1980, 21, 3841. (d) Terao, Y.; Imai, N.; Achiwa, K.; Sekiya, M. Chem. Pharm. Bull. 1982, 30, 3167. (e) Hart, D. J.; Yang, T.-K. Tetrahedron Lett. 1982, 23, 2761. (f) Blum, Z.; Ekstroem, M,; Wistrand, L. G. Acta Chem. Scand., Ser. B 1984, B38, 297. (g) Kametani, T.; Higashiyama, K.; Otomasu, H.; Honda, T. Heterocycles 1984, 22, 729. (h) Shono, T.; Matsumara, Y.; Uchida, K.; Tsubata, K.; Makino, A. J. Org. Chem. 1984, 49, 300. (i) Chamberlin, A. R.; Nguyen, H. D.; Chung, J. Y. L. J. Am. Chem. Soc. 1984, 49, 1682. (j) Hudlicky, T.; Frazier, J. O.; Seoane, G.; Tiedje. M.;  Seoane, A.; Kwart, L. D.; Beal, C. J. Am. Chem. Soc. 1986, 108, 3755. (k) Kametani, T.; Yukawa, H.; Honda, T. J. Chem. Soc., Chem. Commun. 1986, 651.
    • (1977) J. Am. Chem. Soc. , vol.4783 , Issue.99
    • Danishefsky, S.1    McKee, R.2    Singh, R.K.3
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    • Recent chiral syntheses of pyrrolizidine alkaloids: From L-proline derivatives, see: (a) (b) Rüeger, H.; Benn, M. Heterocycles 1982, 19, 1677. (c) Ishibashi, H.; Ozeki, H.; Ikeda, M. J. Chem. Soc., Chem. Commun. 1986, 654. (d) Rüeger, H.; Benn, M. Heterocycles 1982, 19, 23. (e) Rüeger, H.; Benn, M. J. Am. Chem. Soc. 1983, 20, 235. (f) Yadav, V. K.; Rüeger, H.; Benn, M. J. Am. Chem. Soc. 1984, 22, 2735. From (R)-or (S)-malic acid: (g) Chamberlin, A. R.; Chung, J. Y. L. J. Am. Chem. Soc. 1983, 105, 3653. (h) Chamberlin, A. R.; Chung, J. Y. L. J. Org. Chem. 1985, 50, 4425. (i) Hart, D. J. Yang, T.-K. J. Chem. Soc., Chem. Commun. 1983, 135. (j) Hart, D. J. Yang, T.-K. J. Org. Chem. 1985, 50, 235, (k) Choi, J.-K.; Hart, D. J. Tetrahedron 1985, 41, 3959. (i) Niwa, H.; Mirachi, Y.; Okamoto, O.; Uosaki, Y.; Yamada, K. Tetrahedron Lett. 1986, 27, 4605. (m) Shishido, K.; Sukegawa, Y.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1987, 993. From carbohydrates, see: (n) Tatsuta, K.; Takahashi, H.; Amemiya, Y.; Kinoshita, M. J. Am. Chem. Soc. 1983, 105, 4096. (o) Buchanan, J. G.; Singh, G.; Wightman, R. H. J. Chem. Soc., Chem. Commun. 1984, 1299. (p) Nishimura, Y.; Kondo, S.; Umezawa, H. J. Org. Chem. 1985, 50, 5210
    • Recent chiral syntheses of pyrrolizidine alkaloids: From L-proline derivatives, see: (a) Robins, D. J,; Sakdarat, S. J. Chem. Soc. Perkin. Trans. 1 1981, 909. (b) Rüeger, H.; Benn, M. Heterocycles 1982, 19, 1677. (c) Ishibashi, H.; Ozeki, H.; Ikeda, M. J. Chem. Soc., Chem. Commun. 1986, 654. (d) Rüeger, H.; Benn, M. Heterocycles 1982, 19, 23. (e) Rüeger, H.; Benn, M. J. Am. Chem. Soc. 1983, 20, 235. (f) Yadav, V. K.; Rüeger, H.; Benn, M. J. Am. Chem. Soc. 1984, 22, 2735. From (R)-or (S)-malic acid: (g) Chamberlin, A. R.; Chung, J. Y. L. J. Am. Chem. Soc. 1983, 105, 3653. (h) Chamberlin, A. R.; Chung, J. Y. L. J. Org. Chem. 1985, 50, 4425. (i) Hart, D. J. Yang, T.-K. J. Chem. Soc., Chem. Commun. 1983, 135. (j) Hart, D. J. Yang, T.-K. J. Org. Chem. 1985, 50, 235, (k) Choi, J.-K.; Hart, D. J. Tetrahedron 1985, 41, 3959. (i) Niwa, H.; Mirachi, Y.; Okamoto, O.; Uosaki, Y.; Yamada, K. Tetrahedron Lett. 1986, 27, 4605. (m) Shishido, K.; Sukegawa, Y.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1987, 993. From carbohydrates, see: (n) Tatsuta, K.; Takahashi, H.; Amemiya, Y.; Kinoshita, M. J. Am. Chem. Soc. 1983, 105, 4096. (o) Buchanan, J. G.; Singh, G.; Wightman, R. H. J. Chem. Soc., Chem. Commun. 1984, 1299. (p) Nishimura, Y.; Kondo, S.; Umezawa, H. J. Org. Chem. 1985, 50, 5210.
    • (1981) J. Chem. Soc. Perkin. Trans. 1 , pp. 909
    • Robins, D.J.1    Sakdarat, S.2
  • 7
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    • There has been only one paper concerned with the chiral synthesis of (+)-trachelanthamidine (33% op) without the use of the chiral building
    • There has been only one paper concerned with the chiral synthesis of (+)-trachelanthamidine (33% op) without the use of the chiral building Takano, S.; Ogawa, N.; Ogasawara, k. Heterocycles 1981, 16, 915
    • (1981) Heterocycles , vol.915 , Issue.16
    • Takano, S.1    Ogawa, N.2    Ogasawara, k.3
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    • Our recent successful work on the chiral alkylation to 4-acetoxy-2-azetidinones, see: (a) (b) Nagao, Y. Perspective in the Organic Chemistry of Sulfur; Zwanenburg, B., Klunder, A. J. H., Eds.; Elsevier: Amsterdam, 1987; p 57.
    • Our recent successful work on the chiral alkylation to 4-acetoxy-2-azetidinones, see: (a) Nagao, Y.; Kumagai, T.; Tamai, S.; Abe, T.; Kuramoto, Y.; Taga, T.; Aoyagi, S.; Nagase, Y.; Ochiai, M.; Inoue, Y.; Fujita, E. J. Am. Chem. Soc. 1986, 108, 4673. (b) Nagao, Y. Perspective in the Organic Chemistry of Sulfur; Zwanenburg, B., Klunder, A. J. H., Eds.; Elsevier: Amsterdam, 1987; p 57.
    • (1986) J. Am. Chem. Soc , vol.108 , pp. 4673
    • Nagao, Y.1    Kumagai, T.2    Tamai, S.3    Abe, T.4    Kuramoto, Y.5    Taga, T.6    Aoyagi, S.7    Nagase, Y.8    Ochiai, M.9    Inoue, Y.10    Fujita, E.11
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    • For chiral α-amidoalkylation of optically active N-acyliminium with achiral nucleophiles, see
    • For chiral α-amidoalkylation of optically active N-acyliminium with achiral nucleophiles, see: Wanner, K. T.; Kärtner, A. Heterocycles 1987, 26, 921.
    • (1987) Heterocycles , vol.26 , pp. 921
    • Wanner, K.T.1    Kärtner, A.2
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    • (b) Nagasaka, T.; Abe, M.; Ozawa, N.; Kosugi, Y.; Hamaguchi, F. Heterocycles 1983, 20, 985.
    • Hubert, J. C.; Wijnberg, J. B. P. A.; Speckamp, W. N. Tetrahedron 1975, 31, 1437. (b) Nagasaka, T.; Abe, M.; Ozawa, N.; Kosugi, Y.; Hamaguchi, F. Heterocycles 1983, 20, 985.
    • (1975) Tetrahedron , vol.31 , pp. 1437
    • Hubert, J.C.1    Wijnberg, J.B.P.A.2    Speckamp, W.N.3
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    • This reduction can be readily monitored by the disappearance of the original yellow color of the solution. Cf
    • This reduction can be readily monitored by the disappearance of the original yellow color of the solution. Cf. Nagao, Y.; Kawabata, K.; Seno, K.; Fujita, E. J. Chem. Soc., Perkin Trans. 1 1980, 2470.
    • (1980) J. Chem. Soc., Perkin Trans. 1 , pp. 2470
    • Nagao, Y.1    Kawabata, K.2    Seno, K.3    Fujita, E.4
  • 16
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    • Recent reports on the (±)-epilupinine synthesis: (a) and references cited therein. (b) Bremmer, M. L.; Khatri, N. A.; Weinreb, S. M. J. Org. Chem. 1983, 48, 3661. (c) Okita, M.; Wakamatsu, T.; Ban, Y. Heterocycles 1983, 20, 401. (d) Hiemstra, H.; Sno, M. H. A. M.; Vijn, R. J.; Speckamp, W. N. J. Org. Chem. 1985, 50, 4014. (e) Ihara, M.; Kirihara, T.; Fukumoto, K. Heterocycles 1985, 23, 1097. (f) Takahata, H.; Yamabe, K.; Suzuki, T.; Yamazaki, T. J. Am. Chem. Soc. 1986, 24, 37. (g) Comins, D. L.; Brown, J. D. Tetrahedron Lett. 1986, 27, 2219
    • Recent reports on the (±)-epilupinine synthesis: (a) Tufariello, J. J.; Tegeler, J. J. Tetrahedron Lett. 1976, 4037 and references cited therein. (b) Bremmer, M. L.; Khatri, N. A.; Weinreb, S. M. J. Org. Chem. 1983, 48, 3661. (c) Okita, M.; Wakamatsu, T.; Ban, Y. Heterocycles 1983, 20, 401. (d) Hiemstra, H.; Sno, M. H. A. M.; Vijn, R. J.; Speckamp, W. N. J. Org. Chem. 1985, 50, 4014. (e) Ihara, M.; Kirihara, T.; Fukumoto, K. Heterocycles 1985, 23, 1097. (f) Takahata, H.; Yamabe, K.; Suzuki, T.; Yamazaki, T. J. Am. Chem. Soc. 1986, 24, 37. (g) Comins, D. L.; Brown, J. D. Tetrahedron Lett. 1986, 27, 2219.
    • (1976) J. Tetrahedron Lett. , pp. 4037
    • Tufariello, J.J.1    Tegeler, J.2


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