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Volumn 61, Issue 20, 1996, Pages 7106-7115

Total synthesis of (±)-deethylibophyllidine: Studies of a Fischer indolization route and a successful approach via a Pummerer rearrangement/thionium ion-mediated indole cyclization

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; DEETHYLIBOPHYLLIDINE; INDOLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0029822041     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960848z     Document Type: Article
Times cited : (62)

References (91)
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    • For approaches leading to 1,2,3,3a,4,5-hexahydroindol-6-ones, see: (a) from 1,3-cyclohexanedione, Bryson, T. A.; Gammill, R. B. Tetrahedron Lett. 1974, 3963. (b) From 6-methoxyindoline, Iida, H.; Aoyagi, S.; Kibayashi J. Chem. Soc., Perkin Trans. 1 1975, 2502. Iida, H.; Yuasa, Y.; Kibayashi, C. Synthesis 1977, 879. From pyrrolidine-2-thiones, Michael, J. P.; Howard, A. S.; Katz, R. B.; Zwane, M. I. Tetrahedron Lett. 1992, 33, 4751. Michael, J. P.; Zwane, M. I. Tetrahedron Lett. 1992, 33, 4755. For the reduction to octahydroderivatives: Higashiyama, H.; Honda, T.; Otomasu, H.; Kametani, T. Planta Med. 1983, 48, 268. Ito, K.; Naruma, M.; Furukawa, H. J. Chem. Soc., Chem. Commun. 1975, 681.
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    • For approaches leading to 1,2,3,3a,4,5-hexahydroindol-6-ones, see: (a) from 1,3-cyclohexanedione, Bryson, T. A.; Gammill, R. B. Tetrahedron Lett. 1974, 3963. (b) From 6-methoxyindoline, Iida, H.; Aoyagi, S.; Kibayashi J. Chem. Soc., Perkin Trans. 1 1975, 2502. Iida, H.; Yuasa, Y.; Kibayashi, C. Synthesis 1977, 879. From pyrrolidine-2-thiones, Michael, J. P.; Howard, A. S.; Katz, R. B.; Zwane, M. I. Tetrahedron Lett. 1992, 33, 4751. Michael, J. P.; Zwane, M. I. Tetrahedron Lett. 1992, 33, 4755. For the reduction to octahydroderivatives: Higashiyama, H.; Honda, T.; Otomasu, H.; Kametani, T. Planta Med. 1983, 48, 268. Ito, K.; Naruma, M.; Furukawa, H. J. Chem. Soc., Chem. Commun. 1975, 681.
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    • For approaches leading to 1,2,3,3a,4,5-hexahydroindol-6-ones, see: (a) from 1,3-cyclohexanedione, Bryson, T. A.; Gammill, R. B. Tetrahedron Lett. 1974, 3963. (b) From 6-methoxyindoline, Iida, H.; Aoyagi, S.; Kibayashi J. Chem. Soc., Perkin Trans. 1 1975, 2502. Iida, H.; Yuasa, Y.; Kibayashi, C. Synthesis 1977, 879. From pyrrolidine-2-thiones, Michael, J. P.; Howard, A. S.; Katz, R. B.; Zwane, M. I. Tetrahedron Lett. 1992, 33, 4751. Michael, J. P.; Zwane, M. I. Tetrahedron Lett. 1992, 33, 4755. For the reduction to octahydroderivatives: Higashiyama, H.; Honda, T.; Otomasu, H.; Kametani, T. Planta Med. 1983, 48, 268. Ito, K.; Naruma, M.; Furukawa, H. J. Chem. Soc., Chem. Commun. 1975, 681.
    • (1977) Synthesis , pp. 879
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    • For approaches leading to 1,2,3,3a,4,5-hexahydroindol-6-ones, see: (a) from 1,3-cyclohexanedione, Bryson, T. A.; Gammill, R. B. Tetrahedron Lett. 1974, 3963. (b) From 6-methoxyindoline, Iida, H.; Aoyagi, S.; Kibayashi J. Chem. Soc., Perkin Trans. 1 1975, 2502. Iida, H.; Yuasa, Y.; Kibayashi, C. Synthesis 1977, 879. From pyrrolidine-2-thiones, Michael, J. P.; Howard, A. S.; Katz, R. B.; Zwane, M. I. Tetrahedron Lett. 1992, 33, 4751. Michael, J. P.; Zwane, M. I. Tetrahedron Lett. 1992, 33, 4755. For the reduction to octahydroderivatives: Higashiyama, H.; Honda, T.; Otomasu, H.; Kametani, T. Planta Med. 1983, 48, 268. Ito, K.; Naruma, M.; Furukawa, H. J. Chem. Soc., Chem. Commun. 1975, 681.
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    • Michael, J.P.1    Howard, A.S.2    Katz, R.B.3    Zwane, M.I.4
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    • For approaches leading to 1,2,3,3a,4,5-hexahydroindol-6-ones, see: (a) from 1,3-cyclohexanedione, Bryson, T. A.; Gammill, R. B. Tetrahedron Lett. 1974, 3963. (b) From 6-methoxyindoline, Iida, H.; Aoyagi, S.; Kibayashi J. Chem. Soc., Perkin Trans. 1 1975, 2502. Iida, H.; Yuasa, Y.; Kibayashi, C. Synthesis 1977, 879. From pyrrolidine-2-thiones, Michael, J. P.; Howard, A. S.; Katz, R. B.; Zwane, M. I. Tetrahedron Lett. 1992, 33, 4751. Michael, J. P.; Zwane, M. I. Tetrahedron Lett. 1992, 33, 4755. For the reduction to octahydroderivatives: Higashiyama, H.; Honda, T.; Otomasu, H.; Kametani, T. Planta Med. 1983, 48, 268. Ito, K.; Naruma, M.; Furukawa, H. J. Chem. Soc., Chem. Commun. 1975, 681.
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    • note
    • All synthetic compounds are racemic. The schemes depict only the enantiomer bearing the natural configuration at C-14.
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    • 10a For the synthesis of hexahydroindol-6-ones by hypervalent iodine oxidation of tyramine derivatives, see: (a) Kita, Y.; Tohma, H.; Kikuchi, K.; Inagaki, M.; Yakura, T. J. Org. Chem. 1991, 56, 435. (b) Goldstein, D. M.; Wipf, P. Tetrahedron Lett. 1996, 37, 739.
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    • 10a For the synthesis of hexahydroindol-6-ones by hypervalent iodine oxidation of tyramine derivatives, see: (a) Kita, Y.; Tohma, H.; Kikuchi, K.; Inagaki, M.; Yakura, T. J. Org. Chem. 1991, 56, 435. (b) Goldstein, D. M.; Wipf, P. Tetrahedron Lett. 1996, 37, 739.
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    • note
    • On the contrary, when the acylation was carried out in the Schotten-Baumann conditions, acylated but not cyclized compound 3 was isolated (see Experimental Section).
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    • For indolization upon the methine carbon in the Aspidosperma series, see: (a) Stork. G.; Dolfini, J. E. J. Am. Chem. Soc. 1963, 85, 2872. (b) Ban, Y.; Sato, Y.; Inoue, I.; Nagai, M.; Oishi, T.; Terashima, M.; Yonemitsu, O.; Kanaoka, Y. Tetrahedron Lett. 1966, 2261. (c) Inoue, I.; Ban, Y. J. Chem. Soc (C) 1970, 602. (d) Klioze, S. S.; Darmory, F. P. J. Org. Chem. 1975, 40, 1588. (e) Lawton, G.; Saxton, J. E.; Smith, A. J. Tetrahedron 1977, 33, 1641. (f) Pearson, A. J.; Rees, D. C. J. Chem. Soc., Perkin Trans. 1 1982, 2467.
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    • For indolization upon the methine carbon in the Aspidosperma series, see: (a) Stork. G.; Dolfini, J. E. J. Am. Chem. Soc. 1963, 85, 2872. (b) Ban, Y.; Sato, Y.; Inoue, I.; Nagai, M.; Oishi, T.; Terashima, M.; Yonemitsu, O.; Kanaoka, Y. Tetrahedron Lett. 1966, 2261. (c) Inoue, I.; Ban, Y. J. Chem. Soc (C) 1970, 602. (d) Klioze, S. S.; Darmory, F. P. J. Org. Chem. 1975, 40, 1588. (e) Lawton, G.; Saxton, J. E.; Smith, A. J. Tetrahedron 1977, 33, 1641. (f) Pearson, A. J.; Rees, D. C. J. Chem. Soc., Perkin Trans. 1 1982, 2467.
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    • For indolization upon the methine carbon in the Aspidosperma series, see: (a) Stork. G.; Dolfini, J. E. J. Am. Chem. Soc. 1963, 85, 2872. (b) Ban, Y.; Sato, Y.; Inoue, I.; Nagai, M.; Oishi, T.; Terashima, M.; Yonemitsu, O.; Kanaoka, Y. Tetrahedron Lett. 1966, 2261. (c) Inoue, I.; Ban, Y. J. Chem. Soc (C) 1970, 602. (d) Klioze, S. S.; Darmory, F. P. J. Org. Chem. 1975, 40, 1588. (e) Lawton, G.; Saxton, J. E.; Smith, A. J. Tetrahedron 1977, 33, 1641. (f) Pearson, A. J.; Rees, D. C. J. Chem. Soc., Perkin Trans. 1 1982, 2467.
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    • For indolization upon the methine carbon in the Aspidosperma series, see: (a) Stork. G.; Dolfini, J. E. J. Am. Chem. Soc. 1963, 85, 2872. (b) Ban, Y.; Sato, Y.; Inoue, I.; Nagai, M.; Oishi, T.; Terashima, M.; Yonemitsu, O.; Kanaoka, Y. Tetrahedron Lett. 1966, 2261. (c) Inoue, I.; Ban, Y. J. Chem. Soc (C) 1970, 602. (d) Klioze, S. S.; Darmory, F. P. J. Org. Chem. 1975, 40, 1588. (e) Lawton, G.; Saxton, J. E.; Smith, A. J. Tetrahedron 1977, 33, 1641. (f) Pearson, A. J.; Rees, D. C. J. Chem. Soc., Perkin Trans. 1 1982, 2467.
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    • For indolization upon the methine carbon in the Aspidosperma series, see: (a) Stork. G.; Dolfini, J. E. J. Am. Chem. Soc. 1963, 85, 2872. (b) Ban, Y.; Sato, Y.; Inoue, I.; Nagai, M.; Oishi, T.; Terashima, M.; Yonemitsu, O.; Kanaoka, Y. Tetrahedron Lett. 1966, 2261. (c) Inoue, I.; Ban, Y. J. Chem. Soc (C) 1970, 602. (d) Klioze, S. S.; Darmory, F. P. J. Org. Chem. 1975, 40, 1588. (e) Lawton, G.; Saxton, J. E.; Smith, A. J. Tetrahedron 1977, 33, 1641. (f) Pearson, A. J.; Rees, D. C. J. Chem. Soc., Perkin Trans. 1 1982, 2467.
    • (1982) J. Chem. Soc., Perkin Trans. 1 , pp. 2467
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    • See also ref 23e
    • (a) For interesting mechanistic aspects on the Fischer indolization upon β-amino ketones in this field, see: Ban, Y.; Iijima, I. Tetrahedron Lett. 1969, 2523. See also ref 23e.
    • (1969) Tetrahedron Lett. , pp. 2523
    • Ban, Y.1    Iijima, I.2
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    • (b) For a discussion about the stereochemical factors influencing the regiochemical course of Fischer indole synthesis, see: Freter, K.; Fuchs, V.; Pitner, T. P. J. Org. Chem. 1983, 48, 4593.
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    • Freter, K.1    Fuchs, V.2    Pitner, T.P.3
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    • For conformational analysis of the cis-octahydroindole, see: Mokotoff, M.; Hill, S. T. J. Heterocycl. Chem. 1988, 25, 65. For the conformational preference in 3a-aryloctahydroindol-6-ones (i.e. mesembrine), see: Jeffs, P. W.; Hawks, R. L.; Farrier, D. S. J. Am. Chem. Soc. 1969, 91, 3831. Sánchez, I. H.; Larraza, M.-I.; Flores, H. J.; Díaz, E. Heterocycles 1985, 23, 593.
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    • Mokotoff, M.1    Hill, S.T.2
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    • For conformational analysis of the cis-octahydroindole, see: Mokotoff, M.; Hill, S. T. J. Heterocycl. Chem. 1988, 25, 65. For the conformational preference in 3a-aryloctahydroindol-6-ones (i.e. mesembrine), see: Jeffs, P. W.; Hawks, R. L.; Farrier, D. S. J. Am. Chem. Soc. 1969, 91, 3831. Sánchez, I. H.; Larraza, M.-I.; Flores, H. J.; Díaz, E. Heterocycles 1985, 23, 593.
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    • Jeffs, P.W.1    Hawks, R.L.2    Farrier, D.S.3
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    • For conformational analysis of the cis-octahydroindole, see: Mokotoff, M.; Hill, S. T. J. Heterocycl. Chem. 1988, 25, 65. For the conformational preference in 3a-aryloctahydroindol-6-ones (i.e. mesembrine), see: Jeffs, P. W.; Hawks, R. L.; Farrier, D. S. J. Am. Chem. Soc. 1969, 91, 3831. Sánchez, I. H.; Larraza, M.-I.; Flores, H. J.; Díaz, E. Heterocycles 1985, 23, 593.
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    • Sánchez, I.H.1    Larraza, M.-I.2    Flores, H.J.3    Díaz, E.4
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    • N-Benzyliodoacetamide was prepared from benzylamine and chloroacetyl chloride and later treatment of the resulting chlorocetamide with sodium iodide in 2-butanone according to Dufour, M.; Gramain, J.-C.; Husson, H.-P.; Sinibaldi, M.-E.; Troin, Y. J. Org. Chem. 1990, 55, 5483.
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    • note
    • Operating with AcOH/NaOAc or EtOH/HCl instead of AcOH neat, the ratio of indole 17 increases and is the major product in the indolization.
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    • The influence of the A 1,3 strain (Johnson, F. Chem. Rev. 1968, 68, 375) caused by the amide linkage in this conformational change was suggested by a reviewer. Also the difference in regioselectivity in the Fischer indole synthesis of hydroindolones could be accounted for considering that it occurs through the enehydrazine that minimizes the A 1,3 strain.
    • (1968) Chem. Rev. , vol.68 , pp. 375
    • Johnson, F.1
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    • note
    • 13C NMR, see Table 2.
  • 65
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    • note
    • 3, HMQC) 18.4 (C-4), 23.6 (C-5), 26.4 (C-3), 29.7 (C-11), 36.7 (C-3a), 46.4 (C-2), 54.8 (C-10c), 109.6 (C-7), 110.0 (C-10b), 119.0 (C-9), 122.7 (C-8), 124.3 (C-10a), 126.2 (C-10), 131.2 (C-5a), 135.2 (C-6a), 170.4 (C-12).
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    • Trost, B. M., Ed.; Pergamon: Oxford
    • The Pummerer rearrangement has emerged as a versatile and effective method for the generation of cationic reactive intermediates from sulfoxide precursors. For recent reviews, see: (a) Grierson, D. S.; Husson, H.-P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 6, pp 909-947. (b) Kennedy, M.; McKervey, M. A. Ibid. Vol. 7, pp 193-216. (c) De Lucchi, O.; Miotti, U.; Modena, G. Org. React. 1991, 40, 157-405.
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    • Grierson, D.S.1    Husson, H.-P.2
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    • The Pummerer rearrangement has emerged as a versatile and effective method for the generation of cationic reactive intermediates from sulfoxide precursors. For recent reviews, see: (a) Grierson, D. S.; Husson, H.-P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 6, pp 909-947. (b) Kennedy, M.; McKervey, M. A. Ibid. Vol. 7, pp 193-216. (c) De Lucchi, O.; Miotti, U.; Modena, G. Org. React. 1991, 40, 157-405.
    • Comprehensive Organic Synthesis , vol.7 , pp. 193-216
    • Kennedy, M.1    McKervey, M.A.2
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    • The Pummerer rearrangement has emerged as a versatile and effective method for the generation of cationic reactive intermediates from sulfoxide precursors. For recent reviews, see: (a) Grierson, D. S.; Husson, H.-P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 6, pp 909-947. (b) Kennedy, M.; McKervey, M. A. Ibid. Vol. 7, pp 193-216. (c) De Lucchi, O.; Miotti, U.; Modena, G. Org. React. 1991, 40, 157-405.
    • (1991) Org. React. , vol.40 , pp. 157-405
    • De Lucchi, O.1    Miotti, U.2    Modena, G.3
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    • 40c,d upon phenyl vinyl sulfoxide, see: (a) Abbott, D. J.; Colonna, S.; Stirling, C. J. M. J. Chem. Soc., Perkin Trans. 1 1976, 492. (b) Maignan, C.; Guessous, A.; Rouessac, F. Tetrahedron Lett. 1986, 27, 2603. (c) Lee, A. W. M.; Chan, W. H.; Chan, E. T. T. J. Chem. Soc., Perkin Trans. 1 1992, 309. (d) Craig, D.; Daniels, K.; MacKenzie, A. R. Tetrahedron 1992, 48, 7803.
    • (1976) J. Chem. Soc., Perkin Trans. 1 , pp. 492
    • Abbott, D.J.1    Colonna, S.2    Stirling, C.J.M.3
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    • 40c,d upon phenyl vinyl sulfoxide, see: (a) Abbott, D. J.; Colonna, S.; Stirling, C. J. M. J. Chem. Soc., Perkin Trans. 1 1976, 492. (b) Maignan, C.; Guessous, A.; Rouessac, F. Tetrahedron Lett. 1986, 27, 2603. (c) Lee, A. W. M.; Chan, W. H.; Chan, E. T. T. J. Chem. Soc., Perkin Trans. 1 1992, 309. (d) Craig, D.; Daniels, K.; MacKenzie, A. R. Tetrahedron 1992, 48, 7803.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 2603
    • Maignan, C.1    Guessous, A.2    Rouessac, F.3
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    • 40c,d upon phenyl vinyl sulfoxide, see: (a) Abbott, D. J.; Colonna, S.; Stirling, C. J. M. J. Chem. Soc., Perkin Trans. 1 1976, 492. (b) Maignan, C.; Guessous, A.; Rouessac, F. Tetrahedron Lett. 1986, 27, 2603. (c) Lee, A. W. M.; Chan, W. H.; Chan, E. T. T. J. Chem. Soc., Perkin Trans. 1 1992, 309. (d) Craig, D.; Daniels, K.; MacKenzie, A. R. Tetrahedron 1992, 48, 7803.
    • (1992) J. Chem. Soc., Perkin Trans. 1 , pp. 309
    • Lee, A.W.M.1    Chan, W.H.2    Chan, E.T.T.3
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    • 40c,d upon phenyl vinyl sulfoxide, see: (a) Abbott, D. J.; Colonna, S.; Stirling, C. J. M. J. Chem. Soc., Perkin Trans. 1 1976, 492. (b) Maignan, C.; Guessous, A.; Rouessac, F. Tetrahedron Lett. 1986, 27, 2603. (c) Lee, A. W. M.; Chan, W. H.; Chan, E. T. T. J. Chem. Soc., Perkin Trans. 1 1992, 309. (d) Craig, D.; Daniels, K.; MacKenzie, A. R. Tetrahedron 1992, 48, 7803.
    • (1992) Tetrahedron , vol.48 , pp. 7803
    • Craig, D.1    Daniels, K.2    MacKenzie, A.R.3
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    • note
    • Compound 30 was a diastereomeric mixture at sulfur, which could not be separated at this stage.
  • 80
    • 16044370300 scopus 로고    scopus 로고
    • note
    • 42d
  • 85
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    • 7 bond in the synthesis of Aspidosperma alkaloids, but using either an exocyclic or an endocyclic amide as the substrate: Gallagher, T.; Magnus, P.; Huffman, J. C. J. Am. Chem. Soc. 1983, 105, 4750.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 4750
    • Gallagher, T.1    Magnus, P.2    Huffman, J.C.3


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