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Volumn 7, Issue 7, 2005, Pages 1339-1342

An aza-wittig/π-furan cyclization approach toward the homoerythrina alkaloid (±)-selaginoidine

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ALKALOID DERIVATIVE; AZIDE; FURAN DERIVATIVE; HETEROCYCLIC COMPOUND; INDOLE DERIVATIVE; LACTAM DERIVATIVE; PHOSPHORANE DERIVATIVE; SELAGINOIDINE; TRIBUTYLPHOSPHINE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

EID: 17444423725     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0501323     Document Type: Article
Times cited : (34)

References (41)
  • 1
    • 17444405504 scopus 로고
    • Tasmanian Government Printer: Hobart
    • Curtis, W. M. The Student's Flora of Tasmania, Part I; Tasmanian Government Printer: Hobart, 1956; p 6.
    • (1956) The Student's Flora of Tasmania , Issue.1 PART , pp. 6
    • Curtis, W.M.1
  • 4
    • 77956830705 scopus 로고    scopus 로고
    • Cordell, G. A., Ed.; Academic Press: San Diego
    • Tsuda, Y.; Sano, T. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 1996; Vol. 48, pp 249-337.
    • (1996) The Alkaloids , vol.48 , pp. 249-337
    • Tsuda, Y.1    Sano, T.2
  • 12
    • 0000648778 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K.
    • (b) Gilchrist, T. L. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 8, pp 381-402.
    • (1991) Comprehensive Organic Synthesis , vol.8 , pp. 381-402
    • Gilchrist, T.L.1
  • 13
    • 0040834769 scopus 로고
    • Georg-Thieme Verlag: Stuttgart, Germany
    • (c) Hassner, A. In Houben-Weyl Methods of Organic Chemistry, 4th ed.; Georg-Thieme Verlag: Stuttgart, Germany, 1990; Vol. E16a, Part 2, pp 1243-1290.
    • (1990) Houben-Weyl Methods of Organic Chemistry, 4th Ed. , vol.E16A , Issue.2 PART , pp. 1243-1290
    • Hassner, A.1
  • 15
    • 0028204919 scopus 로고
    • For some recent methods, see: (a) Rao, H. S. P.; Siva, P. Synth. Commun. 1994, 24, 549. (b) Ranu, B. C.; Sarkar, A.; Chakraborty, R. J. Org. Chem. 1994, 59, 4114. (c) Alvarez, S. G.; Fisher, G. B.; Singaram, B. Tetrahedron Lett. 1995, 36, 2567. (d) Salunkhe, A. M.; Brown, H. C. Tetrahedron Lett. 1995, 36, 7987. (e) Capperucci, A.; Degl'Innocenti, A.; Funicello, M.; Mauriello, G.; Scafato, P.; Spagnolo, P. J. Org. Chem. 1995, 60, 2254. (f) Goulaouic-Dubois, G.; Hesse, M. Tetrahedron Lett. 1995, 36, 7427. (h) Ramesha, A. R.; Bhat, S.; Chandrasekaran, S. J. Org. Chem. 1995, 60, 7682. (i) Baruah, M.; Boruah, A.; Prajapati, D.; Sandhu, J. S.; Ghosh, A. C. Tetrahedron Lett. 1996, 37, 4559. (j) Peters, R. G.; Warner, B. P.; Burns, C. J. J. Am. Chem. Soc. 1999, 121, 5585.
    • (1994) Synth. Commun. , vol.24 , pp. 549
    • Rao, H.S.P.1    Siva, P.2
  • 16
    • 33751158821 scopus 로고
    • For some recent methods, see: (a) Rao, H. S. P.; Siva, P. Synth. Commun. 1994, 24, 549. (b) Ranu, B. C.; Sarkar, A.; Chakraborty, R. J. Org. Chem. 1994, 59, 4114. (c) Alvarez, S. G.; Fisher, G. B.; Singaram, B. Tetrahedron Lett. 1995, 36, 2567. (d) Salunkhe, A. M.; Brown, H. C. Tetrahedron Lett. 1995, 36, 7987. (e) Capperucci, A.; Degl'Innocenti, A.; Funicello, M.; Mauriello, G.; Scafato, P.; Spagnolo, P. J. Org. Chem. 1995, 60, 2254. (f) Goulaouic-Dubois, G.; Hesse, M. Tetrahedron Lett. 1995, 36, 7427. (h) Ramesha, A. R.; Bhat, S.; Chandrasekaran, S. J. Org. Chem. 1995, 60, 7682. (i) Baruah, M.; Boruah, A.; Prajapati, D.; Sandhu, J. S.; Ghosh, A. C. Tetrahedron Lett. 1996, 37, 4559. (j) Peters, R. G.; Warner, B. P.; Burns, C. J. J. Am. Chem. Soc. 1999, 121, 5585.
    • (1994) J. Org. Chem. , vol.59 , pp. 4114
    • Ranu, B.C.1    Sarkar, A.2    Chakraborty, R.3
  • 17
    • 0028938145 scopus 로고
    • For some recent methods, see: (a) Rao, H. S. P.; Siva, P. Synth. Commun. 1994, 24, 549. (b) Ranu, B. C.; Sarkar, A.; Chakraborty, R. J. Org. Chem. 1994, 59, 4114. (c) Alvarez, S. G.; Fisher, G. B.; Singaram, B. Tetrahedron Lett. 1995, 36, 2567. (d) Salunkhe, A. M.; Brown, H. C. Tetrahedron Lett. 1995, 36, 7987. (e) Capperucci, A.; Degl'Innocenti, A.; Funicello, M.; Mauriello, G.; Scafato, P.; Spagnolo, P. J. Org. Chem. 1995, 60, 2254. (f) Goulaouic-Dubois, G.; Hesse, M. Tetrahedron Lett. 1995, 36, 7427. (h) Ramesha, A. R.; Bhat, S.; Chandrasekaran, S. J. Org. Chem. 1995, 60, 7682. (i) Baruah, M.; Boruah, A.; Prajapati, D.; Sandhu, J. S.; Ghosh, A. C. Tetrahedron Lett. 1996, 37, 4559. (j) Peters, R. G.; Warner, B. P.; Burns, C. J. J. Am. Chem. Soc. 1999, 121, 5585.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 2567
    • Alvarez, S.G.1    Fisher, G.B.2    Singaram, B.3
  • 18
    • 0028860815 scopus 로고
    • For some recent methods, see: (a) Rao, H. S. P.; Siva, P. Synth. Commun. 1994, 24, 549. (b) Ranu, B. C.; Sarkar, A.; Chakraborty, R. J. Org. Chem. 1994, 59, 4114. (c) Alvarez, S. G.; Fisher, G. B.; Singaram, B. Tetrahedron Lett. 1995, 36, 2567. (d) Salunkhe, A. M.; Brown, H. C. Tetrahedron Lett. 1995, 36, 7987. (e) Capperucci, A.; Degl'Innocenti, A.; Funicello, M.; Mauriello, G.; Scafato, P.; Spagnolo, P. J. Org. Chem. 1995, 60, 2254. (f) Goulaouic-Dubois, G.; Hesse, M. Tetrahedron Lett. 1995, 36, 7427. (h) Ramesha, A. R.; Bhat, S.; Chandrasekaran, S. J. Org. Chem. 1995, 60, 7682. (i) Baruah, M.; Boruah, A.; Prajapati, D.; Sandhu, J. S.; Ghosh, A. C. Tetrahedron Lett. 1996, 37, 4559. (j) Peters, R. G.; Warner, B. P.; Burns, C. J. J. Am. Chem. Soc. 1999, 121, 5585.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 7987
    • Salunkhe A., M.1    Brown, H.C.2
  • 19
    • 0000801310 scopus 로고
    • For some recent methods, see: (a) Rao, H. S. P.; Siva, P. Synth. Commun. 1994, 24, 549. (b) Ranu, B. C.; Sarkar, A.; Chakraborty, R. J. Org. Chem. 1994, 59, 4114. (c) Alvarez, S. G.; Fisher, G. B.; Singaram, B. Tetrahedron Lett. 1995, 36, 2567. (d) Salunkhe, A. M.; Brown, H. C. Tetrahedron Lett. 1995, 36, 7987. (e) Capperucci, A.; Degl'Innocenti, A.; Funicello, M.; Mauriello, G.; Scafato, P.; Spagnolo, P. J. Org. Chem. 1995, 60, 2254. (f) Goulaouic-Dubois, G.; Hesse, M. Tetrahedron Lett. 1995, 36, 7427. (h) Ramesha, A. R.; Bhat, S.; Chandrasekaran, S. J. Org. Chem. 1995, 60, 7682. (i) Baruah, M.; Boruah, A.; Prajapati, D.; Sandhu, J. S.; Ghosh, A. C. Tetrahedron Lett. 1996, 37, 4559. (j) Peters, R. G.; Warner, B. P.; Burns, C. J. J. Am. Chem. Soc. 1999, 121, 5585.
    • (1995) J. Org. Chem. , vol.60 , pp. 2254
    • Capperucci, A.1    Degl'Innocenti, A.2    Funicello, M.3    Mauriello, G.4    Scafato, P.5    Spagnolo, P.6
  • 20
    • 0029100428 scopus 로고
    • For some recent methods, see: (a) Rao, H. S. P.; Siva, P. Synth. Commun. 1994, 24, 549. (b) Ranu, B. C.; Sarkar, A.; Chakraborty, R. J. Org. Chem. 1994, 59, 4114. (c) Alvarez, S. G.; Fisher, G. B.; Singaram, B. Tetrahedron Lett. 1995, 36, 2567. (d) Salunkhe, A. M.; Brown, H. C. Tetrahedron Lett. 1995, 36, 7987. (e) Capperucci, A.; Degl'Innocenti, A.; Funicello, M.; Mauriello, G.; Scafato, P.; Spagnolo, P. J. Org. Chem. 1995, 60, 2254. (f) Goulaouic-Dubois, G.; Hesse, M. Tetrahedron Lett. 1995, 36, 7427. (h) Ramesha, A. R.; Bhat, S.; Chandrasekaran, S. J. Org. Chem. 1995, 60, 7682. (i) Baruah, M.; Boruah, A.; Prajapati, D.; Sandhu, J. S.; Ghosh, A. C. Tetrahedron Lett. 1996, 37, 4559. (j) Peters, R. G.; Warner, B. P.; Burns, C. J. J. Am. Chem. Soc. 1999, 121, 5585.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 7427
    • Goulaouic-Dubois, G.1    Hesse, M.2
  • 21
    • 0001303031 scopus 로고
    • For some recent methods, see: (a) Rao, H. S. P.; Siva, P. Synth. Commun. 1994, 24, 549. (b) Ranu, B. C.; Sarkar, A.; Chakraborty, R. J. Org. Chem. 1994, 59, 4114. (c) Alvarez, S. G.; Fisher, G. B.; Singaram, B. Tetrahedron Lett. 1995, 36, 2567. (d) Salunkhe, A. M.; Brown, H. C. Tetrahedron Lett. 1995, 36, 7987. (e) Capperucci, A.; Degl'Innocenti, A.; Funicello, M.; Mauriello, G.; Scafato, P.; Spagnolo, P. J. Org. Chem. 1995, 60, 2254. (f) Goulaouic-Dubois, G.; Hesse, M. Tetrahedron Lett. 1995, 36, 7427. (h) Ramesha, A. R.; Bhat, S.; Chandrasekaran, S. J. Org. Chem. 1995, 60, 7682. (i) Baruah, M.; Boruah, A.; Prajapati, D.; Sandhu, J. S.; Ghosh, A. C. Tetrahedron Lett. 1996, 37, 4559. (j) Peters, R. G.; Warner, B. P.; Burns, C. J. J. Am. Chem. Soc. 1999, 121, 5585.
    • (1995) J. Org. Chem. , vol.60 , pp. 7682
    • Ramesha, A.R.1    Bhat, S.2    Chandrasekaran, S.3
  • 22
    • 0030600164 scopus 로고    scopus 로고
    • For some recent methods, see: (a) Rao, H. S. P.; Siva, P. Synth. Commun. 1994, 24, 549. (b) Ranu, B. C.; Sarkar, A.; Chakraborty, R. J. Org. Chem. 1994, 59, 4114. (c) Alvarez, S. G.; Fisher, G. B.; Singaram, B. Tetrahedron Lett. 1995, 36, 2567. (d) Salunkhe, A. M.; Brown, H. C. Tetrahedron Lett. 1995, 36, 7987. (e) Capperucci, A.; Degl'Innocenti, A.; Funicello, M.; Mauriello, G.; Scafato, P.; Spagnolo, P. J. Org. Chem. 1995, 60, 2254. (f) Goulaouic-Dubois, G.; Hesse, M. Tetrahedron Lett. 1995, 36, 7427. (h) Ramesha, A. R.; Bhat, S.; Chandrasekaran, S. J. Org. Chem. 1995, 60, 7682. (i) Baruah, M.; Boruah, A.; Prajapati, D.; Sandhu, J. S.; Ghosh, A. C. Tetrahedron Lett. 1996, 37, 4559. (j) Peters, R. G.; Warner, B. P.; Burns, C. J. J. Am. Chem. Soc. 1999, 121, 5585.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 4559
    • Baruah, M.1    Boruah, A.2    Prajapati, D.3    Sandhu, J.S.4    Ghosh, A.C.5
  • 23
    • 0033575069 scopus 로고    scopus 로고
    • For some recent methods, see: (a) Rao, H. S. P.; Siva, P. Synth. Commun. 1994, 24, 549. (b) Ranu, B. C.; Sarkar, A.; Chakraborty, R. J. Org. Chem. 1994, 59, 4114. (c) Alvarez, S. G.; Fisher, G. B.; Singaram, B. Tetrahedron Lett. 1995, 36, 2567. (d) Salunkhe, A. M.; Brown, H. C. Tetrahedron Lett. 1995, 36, 7987. (e) Capperucci, A.; Degl'Innocenti, A.; Funicello, M.; Mauriello, G.; Scafato, P.; Spagnolo, P. J. Org. Chem. 1995, 60, 2254. (f) Goulaouic-Dubois, G.; Hesse, M. Tetrahedron Lett. 1995, 36, 7427. (h) Ramesha, A. R.; Bhat, S.; Chandrasekaran, S. J. Org. Chem. 1995, 60, 7682. (i) Baruah, M.; Boruah, A.; Prajapati, D.; Sandhu, J. S.; Ghosh, A. C. Tetrahedron Lett. 1996, 37, 4559. (j) Peters, R. G.; Warner, B. P.; Burns, C. J. J. Am. Chem. Soc. 1999, 121, 5585.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 5585
    • Peters, R.G.1    Warner, B.P.2    Burns, C.J.3
  • 31
    • 17444399947 scopus 로고    scopus 로고
    • note
    • Unfortunately, all of our attempts to induce a Heck or radical cyclization of 13 failed. We are currently investigating a Lewis acid induced cyclization of the debrominated furan derived from 13.
  • 41
    • 0000646877 scopus 로고
    • Trost, B. M.; Fleming, I.; Eds.; Pergamon Press: Oxford
    • Denmark, S. E. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 751-784.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 751-784
    • Denmark, S.E.1


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