Enantiospecific synthesis of (+)-nemorensic acid, a necic acid component of the macropyrrolizidine alkaloid, nemorensine

Journal of Organic Chemistry

Volumn 64, Issue 15, 1999, Pages 5542-5546

  Honda, Toshio ^a   Ishikawa, Fumihiro ^a  

^a HOSHI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; NEMORENSIC ACID; NEMORENSINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; ENANTIOMER; STEREOSPECIFICITY; SYNTHESIS;

EID: 0033597805     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990366y     Document Type: Article

References (30)

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5. Reviews: (a) Inanaga, J. J. Org. Synth. Chem. 1989, 47, 200. (b) Soderquist, J. A. Aldrichim Acta 1991, 24 15. (c) Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943. (d) Molander, G. A. Chem. Rev. 1992, 92, 29. (e) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (f) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321 and references therein.
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7. Reviews: (a) Inanaga, J. J. Org. Synth. Chem. 1989, 47, 200. (b) Soderquist, J. A. Aldrichim Acta 1991, 24 15. (c) Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943. (d) Molander, G. A. Chem. Rev. 1992, 92, 29. (e) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (f) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321 and references therein.
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15. Only one synthesis of racemic nemorensic acid was so far reported: Klein, L. L. J. Am. Chem. Soc. 1985, 107, 2573.
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17. Mattocks, A. R. Chemistry and Toxicology of Pyrrolizidine Alkaloids; Academic Press: London, 1986.
18. For some examples of the syntheses of macrolactonic pyrrolizidine alkaloids, (a) (+)-Dicrotaline: Devlin, J. A.; Robins, D. J. J. Chem. Soc., Chem. Commun. 1981, 1272. (b) (+)-Dicrotaline: Niwa, H.; Okamoto, O.; Ishiwata, H.; Kuroda, A.; Uosaki, Y.; Yamada, K. Bull. Chem. Soc. Jpn. 1988, 61, 3017. (c) (±)- Fulvine and (±)-crispatine: Vedejs, E.; Larsen, S. D. J. Am. Chem. Soc. 1984, 106, 3030. (d) (±)- Integerrimine: Narasaka, K.; Sakakura, T.; Uchimaru, T.; Guedin- Vuong, D. Ibid. 1984, 106, 2954. (e) (-)-Integerrimine and (+)- usaramine: White, J. D.; Amedio, J. C., Jr.; Gut, S.; Ohira, S.; Jayasinghe, L. R. J. Org. Chem. 1992, 57, 2270. (f) (-)-Integerrimine: Niwa, H.; Machiya, Y.; Okamoto, O.; Uosaki, Y.; Kuroda, A.; Ishiwata, H.; Yamada, K. Tetrahedron 1992, 48, 393. (g) Monocrotaline: Vedejs, E.; Ahmad, S.; Larsen, S. D.; Westwood, S. J. Org. Chem. 1987, 52, 3927. (h) Monocrotaline: Honda, T.; Tomitsuka, K.; Tsubuki, M. J. Org. Chem. 1993, 58, 4274.
19. For some examples of the syntheses of macrolactonic pyrrolizidine alkaloids, (a) (+)-Dicrotaline: Devlin, J. A.; Robins, D. J. J. Chem. Soc., Chem. Commun. 1981, 1272. (b) (+)-Dicrotaline: Niwa, H.; Okamoto, O.; Ishiwata, H.; Kuroda, A.; Uosaki, Y.; Yamada, K. Bull. Chem. Soc. Jpn. 1988, 61, 3017. (c) (±)- Fulvine and (±)-crispatine: Vedejs, E.; Larsen, S. D. J. Am. Chem. Soc. 1984, 106, 3030. (d) (±)- Integerrimine: Narasaka, K.; Sakakura, T.; Uchimaru, T.; Guedin- Vuong, D. Ibid. 1984, 106, 2954. (e) (-)-Integerrimine and (+)- usaramine: White, J. D.; Amedio, J. C., Jr.; Gut, S.; Ohira, S.; Jayasinghe, L. R. J. Org. Chem. 1992, 57, 2270. (f) (-)-Integerrimine: Niwa, H.; Machiya, Y.; Okamoto, O.; Uosaki, Y.; Kuroda, A.; Ishiwata, H.; Yamada, K. Tetrahedron 1992, 48, 393. (g) Monocrotaline: Vedejs, E.; Ahmad, S.; Larsen, S. D.; Westwood, S. J. Org. Chem. 1987, 52, 3927. (h) Monocrotaline: Honda, T.; Tomitsuka, K.; Tsubuki, M. J. Org. Chem. 1993, 58, 4274.
20. For some examples of the syntheses of macrolactonic pyrrolizidine alkaloids, (a) (+)-Dicrotaline: Devlin, J. A.; Robins, D. J. J. Chem. Soc., Chem. Commun. 1981, 1272. (b) (+)-Dicrotaline: Niwa, H.; Okamoto, O.; Ishiwata, H.; Kuroda, A.; Uosaki, Y.; Yamada, K. Bull. Chem. Soc. Jpn. 1988, 61, 3017. (c) (±)- Fulvine and (±)-crispatine: Vedejs, E.; Larsen, S. D. J. Am. Chem. Soc. 1984, 106, 3030. (d) (±)- Integerrimine: Narasaka, K.; Sakakura, T.; Uchimaru, T.; Guedin- Vuong, D. Ibid. 1984, 106, 2954. (e) (-)-Integerrimine and (+)- usaramine: White, J. D.; Amedio, J. C., Jr.; Gut, S.; Ohira, S.; Jayasinghe, L. R. J. Org. Chem. 1992, 57, 2270. (f) (-)-Integerrimine: Niwa, H.; Machiya, Y.; Okamoto, O.; Uosaki, Y.; Kuroda, A.; Ishiwata, H.; Yamada, K. Tetrahedron 1992, 48, 393. (g) Monocrotaline: Vedejs, E.; Ahmad, S.; Larsen, S. D.; Westwood, S. J. Org. Chem. 1987, 52, 3927. (h) Monocrotaline: Honda, T.; Tomitsuka, K.; Tsubuki, M. J. Org. Chem. 1993, 58, 4274.
21. For some examples of the syntheses of macrolactonic pyrrolizidine alkaloids, (a) (+)-Dicrotaline: Devlin, J. A.; Robins, D. J. J. Chem. Soc., Chem. Commun. 1981, 1272. (b) (+)-Dicrotaline: Niwa, H.; Okamoto, O.; Ishiwata, H.; Kuroda, A.; Uosaki, Y.; Yamada, K. Bull. Chem. Soc. Jpn. 1988, 61, 3017. (c) (±)- Fulvine and (±)-crispatine: Vedejs, E.; Larsen, S. D. J. Am. Chem. Soc. 1984, 106, 3030. (d) (±)-Integerrimine: Narasaka, K.; Sakakura, T.; Uchimaru, T.; Guedin-Vuong, D. Ibid. 1984, 106, 2954. (e) (-)-Integerrimine and (+)- usaramine: White, J. D.; Amedio, J. C., Jr.; Gut, S.; Ohira, S.; Jayasinghe, L. R. J. Org. Chem. 1992, 57, 2270. (f) (-)-Integerrimine: Niwa, H.; Machiya, Y.; Okamoto, O.; Uosaki, Y.; Kuroda, A.; Ishiwata, H.; Yamada, K. Tetrahedron 1992, 48, 393. (g) Monocrotaline: Vedejs, E.; Ahmad, S.; Larsen, S. D.; Westwood, S. J. Org. Chem. 1987, 52, 3927. (h) Monocrotaline: Honda, T.; Tomitsuka, K.; Tsubuki, M. J. Org. Chem. 1993, 58, 4274.
22. For some examples of the syntheses of macrolactonic pyrrolizidine alkaloids, (a) (+)-Dicrotaline: Devlin, J. A.; Robins, D. J. J. Chem. Soc., Chem. Commun. 1981, 1272. (b) (+)-Dicrotaline: Niwa, H.; Okamoto, O.; Ishiwata, H.; Kuroda, A.; Uosaki, Y.; Yamada, K. Bull. Chem. Soc. Jpn. 1988, 61, 3017. (c) (±)- Fulvine and (±)-crispatine: Vedejs, E.; Larsen, S. D. J. Am. Chem. Soc. 1984, 106, 3030. (d) (±)- Integerrimine: Narasaka, K.; Sakakura, T.; Uchimaru, T.; Guedin- Vuong, D. Ibid. 1984, 106, 2954. (e) (-)-Integerrimine and (+)-usaramine: White, J. D.; Amedio, J. C., Jr.; Gut, S.; Ohira, S.; Jayasinghe, L. R. J. Org. Chem. 1992, 57, 2270. (f) (-)-Integerrimine: Niwa, H.; Machiya, Y.; Okamoto, O.; Uosaki, Y.; Kuroda, A.; Ishiwata, H.; Yamada, K. Tetrahedron 1992, 48, 393. (g) Monocrotaline: Vedejs, E.; Ahmad, S.; Larsen, S. D.; Westwood, S. J. Org. Chem. 1987, 52, 3927. (h) Monocrotaline: Honda, T.; Tomitsuka, K.; Tsubuki, M. J. Org. Chem. 1993, 58, 4274.
23. For some examples of the syntheses of macrolactonic pyrrolizidine alkaloids, (a) (+)-Dicrotaline: Devlin, J. A.; Robins, D. J. J. Chem. Soc., Chem. Commun. 1981, 1272. (b) (+)-Dicrotaline: Niwa, H.; Okamoto, O.; Ishiwata, H.; Kuroda, A.; Uosaki, Y.; Yamada, K. Bull. Chem. Soc. Jpn. 1988, 61, 3017. (c) (±)- Fulvine and (±)-crispatine: Vedejs, E.; Larsen, S. D. J. Am. Chem. Soc. 1984, 106, 3030. (d) (±)- Integerrimine: Narasaka, K.; Sakakura, T.; Uchimaru, T.; Guedin- Vuong, D. Ibid. 1984, 106, 2954. (e) (-)-Integerrimine and (+)- usaramine: White, J. D.; Amedio, J. C., Jr.; Gut, S.; Ohira, S.; Jayasinghe, L. R. J. Org. Chem. 1992, 57, 2270. (f) (-)-Integerrimine: Niwa, H.; Machiya, Y.; Okamoto, O.; Uosaki, Y.; Kuroda, A.; Ishiwata, H.; Yamada, K. Tetrahedron 1992, 48, 393. (g) Monocrotaline: Vedejs, E.; Ahmad, S.; Larsen, S. D.; Westwood, S. J. Org. Chem. 1987, 52, 3927. (h) Monocrotaline: Honda, T.; Tomitsuka, K.; Tsubuki, M. J. Org. Chem. 1993, 58, 4274.
24. For some examples of the syntheses of macrolactonic pyrrolizidine alkaloids, (a) (+)-Dicrotaline: Devlin, J. A.; Robins, D. J. J. Chem. Soc., Chem. Commun. 1981, 1272. (b) (+)-Dicrotaline: Niwa, H.; Okamoto, O.; Ishiwata, H.; Kuroda, A.; Uosaki, Y.; Yamada, K. Bull. Chem. Soc. Jpn. 1988, 61, 3017. (c) (±)- Fulvine and (±)-crispatine: Vedejs, E.; Larsen, S. D. J. Am. Chem. Soc. 1984, 106, 3030. (d) (±)- Integerrimine: Narasaka, K.; Sakakura, T.; Uchimaru, T.; Guedin- Vuong, D. Ibid. 1984, 106, 2954. (e) (-)-Integerrimine and (+)- usaramine: White, J. D.; Amedio, J. C., Jr.; Gut, S.; Ohira, S.; Jayasinghe, L. R. J. Org. Chem. 1992, 57, 2270. (f) (-)-Integerrimine: Niwa, H.; Machiya, Y.; Okamoto, O.; Uosaki, Y.; Kuroda, A.; Ishiwata, H.; Yamada, K. Tetrahedron 1992, 48, 393. (g) Monocrotaline: Vedejs, E.; Ahmad, S.; Larsen, S. D.; Westwood, S. J. Org. Chem. 1987, 52, 3927. (h) Monocrotaline: Honda, T.; Tomitsuka, K.; Tsubuki, M. J. Org. Chem. 1993, 58, 4274.
25. For some examples of the syntheses of macrolactonic pyrrolizidine alkaloids, (a) (+)-Dicrotaline: Devlin, J. A.; Robins, D. J. J. Chem. Soc., Chem. Commun. 1981, 1272. (b) (+)-Dicrotaline: Niwa, H.; Okamoto, O.; Ishiwata, H.; Kuroda, A.; Uosaki, Y.; Yamada, K. Bull. Chem. Soc. Jpn. 1988, 61, 3017. (c) (±)- Fulvine and (±)-crispatine: Vedejs, E.; Larsen, S. D. J. Am. Chem. Soc. 1984, 106, 3030. (d) (±)- Integerrimine: Narasaka, K.; Sakakura, T.; Uchimaru, T.; Guedin- Vuong, D. Ibid. 1984, 106, 2954. (e) (-)-Integerrimine and (+)- usaramine: White, J. D.; Amedio, J. C., Jr.; Gut, S.; Ohira, S.; Jayasinghe, L. R. J. Org. Chem. 1992, 57, 2270. (f) (-)-Integerrimine: Niwa, H.; Machiya, Y.; Okamoto, O.; Uosaki, Y.; Kuroda, A.; Ishiwata, H.; Yamada, K. Tetrahedron 1992, 48, 393. (g) Monocrotaline: Vedejs, E.; Ahmad, S.; Larsen, S. D.; Westwood, S. J. Org. Chem. 1987, 52, 3927. (h) Monocrotaline: Honda, T.; Tomitsuka, K.; Tsubuki, M. J. Org. Chem. 1993, 58, 4274.
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27. Dillon, M. P.; Lee, N. C.; Stappenbeck, F.; White, J. D. J. Chem. Soc., Chem. Commun. 1995, 1645 and references therein. This is the first and only chiral synthesis of nemorensic acid.
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