A concise synthesis of (-)-codonopsinine and an approach to synthesis of (+)-hyacinthacines A1 and A2 from a polyhydroxylated cyclic nitrone

Synlett

Volumn , Issue 1, 2003, Pages 35-38

  Toyao, Atsushi ^a   Tamura, Osamu ^a   Takagi, Hiroko ^a   Ishibashi, Hiroyuki ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

Cyclic nitrone; Cycloaddition; Natural products; Nucleophilic addition; Total synthesis

Indexed keywords

ALKALOID; CODONOPSININE; HYACINTHACINE A1; HYACINTHACINE A2; NATURAL PRODUCT; NITRONE; PYRROLIZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037242830     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (48)

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11. For recent reviews of syntheses of pyrrolidine and pyrrolizidine alkaloids, see: (a) Liddell, J. R. Nat. Prod. Rep. 1999, 16, 499. (b) Michael, J. P. Nat. Prod. Rep. 1997, 14, 619. (c) Robins, D. J. Nat. Prod. Rep. 1995, 12, 413. (d) For leading references, see: Hulme, A. N.; Rosser, E. M. Org. Lett. 2002, 4, 265. (e) See also: Cordero, F. M.; Pisaneschi, F.; Gensini, M.; Goti, A.; Brandi, A. Eur. J. Org. Chem. 2002, 1941. (f) See also: Severino, E. A.; Correia, C. R. D. Org. Lett. 2000, 2, 3039. (g) See also: Cordero, F. M.; Gensini, M.; Goti, A.; Brandi, A. Org. Lett. 2000, 2, 2475. (h) See also: Yoda, H.; Asai, F.; Takabe, K. Synlett 2000, 1001. (i) See also: Yoda, H.; Katoh, H.; Takabe, K. Tetrahedron Lett. 2000, 41, 7661. (j) See also: Ahn, J.-B.; Yun, C.-S.; Kim, K. H.; Ha, D.-C. J. Org. Chem. 2000, 65, 9249. (k) See also: Pearson, W. H.; Hines, J. V. J. Org. Chem. 2000, 65, 5785. (l)See also: Denmark, S. E.; Herbert, B. J. Org. Chem. 2000, 65, 2887. (m) See also: Denmark, S. E.; Hurd, A. R. Org. Lett. 1999, 1, 1311.
12. For recent reviews of syntheses of pyrrolidine and pyrrolizidine alkaloids, see: (a) Liddell, J. R. Nat. Prod. Rep. 1999, 16, 499. (b) Michael, J. P. Nat. Prod. Rep. 1997, 14, 619. (c) Robins, D. J. Nat. Prod. Rep. 1995, 12, 413. (d) For leading references, see: Hulme, A. N.; Rosser, E. M. Org. Lett. 2002, 4, 265. (e) See also: Cordero, F. M.; Pisaneschi, F.; Gensini, M.; Goti, A.; Brandi, A. Eur. J. Org. Chem. 2002, 1941. (f) See also: Severino, E. A.; Correia, C. R. D. Org. Lett. 2000, 2, 3039. (g) See also: Cordero, F. M.; Gensini, M.; Goti, A.; Brandi, A. Org. Lett. 2000, 2, 2475. (h) See also: Yoda, H.; Asai, F.; Takabe, K. Synlett 2000, 1001. (i) See also: Yoda, H.; Katoh, H.; Takabe, K. Tetrahedron Lett. 2000, 41, 7661. (j) See also: Ahn, J.-B.; Yun, C.-S.; Kim, K. H.; Ha, D.-C. J. Org. Chem. 2000, 65, 9249. (k) See also: Pearson, W. H.; Hines, J. V. J. Org. Chem. 2000, 65, 5785. (l)See also: Denmark, S. E.; Herbert, B. J. Org. Chem. 2000, 65, 2887. (m) See also: Denmark, S. E.; Hurd, A. R. Org. Lett. 1999, 1, 1311.
13. For recent reviews of syntheses of pyrrolidine and pyrrolizidine alkaloids, see: (a) Liddell, J. R. Nat. Prod. Rep. 1999, 16, 499. (b) Michael, J. P. Nat. Prod. Rep. 1997, 14, 619. (c) Robins, D. J. Nat. Prod. Rep. 1995, 12, 413. (d) For leading references, see: Hulme, A. N.; Rosser, E. M. Org. Lett. 2002, 4, 265. (e) See also: Cordero, F. M.; Pisaneschi, F.; Gensini, M.; Goti, A.; Brandi, A. Eur. J. Org. Chem. 2002, 1941. (f) See also: Severino, E. A.; Correia, C. R. D. Org. Lett. 2000, 2, 3039. (g) See also: Cordero, F. M.; Gensini, M.; Goti, A.; Brandi, A. Org. Lett. 2000, 2, 2475. (h) See also: Yoda, H.; Asai, F.; Takabe, K. Synlett 2000, 1001. (i) See also: Yoda, H.; Katoh, H.; Takabe, K. Tetrahedron Lett. 2000, 41, 7661. (j) See also: Ahn, J.-B.; Yun, C.-S.; Kim, K. H.; Ha, D.-C. J. Org. Chem. 2000, 65, 9249. (k) See also: Pearson, W. H.; Hines, J. V. J. Org. Chem. 2000, 65, 5785. (l)See also: Denmark, S. E.; Herbert, B. J. Org. Chem. 2000, 65, 2887. (m) See also: Denmark, S. E.; Hurd, A. R. Org. Lett. 1999, 1, 1311.
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16. For recent reviews of syntheses of pyrrolidine and pyrrolizidine alkaloids, see: (a) Liddell, J. R. Nat. Prod. Rep. 1999, 16, 499. (b) Michael, J. P. Nat. Prod. Rep. 1997, 14, 619. (c) Robins, D. J. Nat. Prod. Rep. 1995, 12, 413. (d) For leading references, see: Hulme, A. N.; Rosser, E. M. Org. Lett. 2002, 4, 265. (e) See also: Cordero, F. M.; Pisaneschi, F.; Gensini, M.; Goti, A.; Brandi, A. Eur. J. Org. Chem. 2002, 1941. (f) See also: Severino, E. A.; Correia, C. R. D. Org. Lett. 2000, 2, 3039. (g) See also: Cordero, F. M.; Gensini, M.; Goti, A.; Brandi, A. Org. Lett. 2000, 2, 2475. (h) See also: Yoda, H.; Asai, F.; Takabe, K. Synlett 2000, 1001. (i) See also: Yoda, H.; Katoh, H.; Takabe, K. Tetrahedron Lett. 2000, 41, 7661. (j) See also: Ahn, J.-B.; Yun, C.-S.; Kim, K. H.; Ha, D.-C. J. Org. Chem. 2000, 65, 9249. (k) See also: Pearson, W. H.; Hines, J. V. J. Org. Chem. 2000, 65, 5785. (l)See also: Denmark, S. E.; Herbert, B. J. Org. Chem. 2000, 65, 2887. (m) See also: Denmark, S. E.; Hurd, A. R. Org. Lett. 1999, 1, 1311.
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29. (c) For recent syntheses of codonopsinine and codonopsine, see: Yoda, H.; Nakajima, T.; Takabe, K. Tetrahedron Lett. 1996, 37, 5531.
30. (d) See also: Wang, C.-L. J.; Calabrese, J. C. J. Org. Chem. 1991, 56, 4341.
31. (e) See further: Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1987, 52, 1956; see also ref. 3f.
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37. 3): δ = 55.7, 65.9, 72.0, 73.5, 77.3, 80.8, 81.8, 96.4, 127.6, 127.7, 127.8, 128.1, 128.3, 128.5, 133.4, 137.2, 137.7.
38. 2, see: Portolés, R.; Murga, J.; Falomir, E.; Carda, M.; Uriel, S.; Marco, J. A. Synlett 2002, 711.
39. (b) For a review of nucleophilic addition to nitrones, see: Lombardo, M.; Trombini, C. Synthesis 2000, 759.
40. 3): δ = 55.2, 55.3, 67.0, 68.8, 71.7, 73.4, 73.5, 83.9, 84.6, 95.6, 113.8, 127.6, 127.7, 127.9, 128.3, 128.4, 129.7, 130.8, 138.2, 138.3, 159.3.
41. 3f.5e
42. For recent reviews of cycloaddition of nitrones, see: (a) Broggini, G.; Zecchi, G. Synthesis 1999, 905. (b) Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863.
43. For recent reviews of cycloaddition of nitrones, see: (a) Broggini, G.; Zecchi, G. Synthesis 1999, 905. (b) Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863.
44. 3): δ = 28.0, 37.8, 55.6, 68.3, 69.8, 70.1, 72.3, 73.4, 75.5, 82.0, 84.3, 85.1, 96.0, 127.5, 127.7, 127.8, 128.2, 128.3, 138.0, 138.3, 169.5.
45. Barton, D. H. R.; Dorchak, J.; Jaszberenyi, J. C. Tetrahedron 1992, 48, 7435.
46. The stereochemistry of compound 15 was established by its NOE difference spectrum shown below.
47. Amide 16 was also obtained from 13c' via three similar steps.
48. 3): δ = 26.3, 33.2, 59.4, 67.5, 71.0, 71.9, 73.8, 81.4, 89.2, 127.7, 127.8, 127.9, 128.1, 128.5, 128.6, 137.6, 138.1, 176.6.