Stereochemical determination of acyclic structures based on carbon- proton spin-coupling constants. A method of configuration analysis for natural products

Journal of Organic Chemistry

Volumn 64, Issue 3, 1999, Pages 866-876

  Matsumori, Nobuaki ^a   Kaneno, Daisuke ^a   Murata, Michio ^a   Nakamura, Hideshi ^b   Tachibana, Kazuo ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4 PHENYL 2,3 DIHYDROXYETHYLACETIC ACID; 4 PHENYL 3 DIHYDROXY 2 METHYLETHYLACETIC ACID; ACETIC ACID DERIVATIVE; NATURAL PRODUCT; ORGANIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033525048     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981810k     Document Type: Article

References (62)

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20. Applications of this methodology to the configuration assignment of natural products have been published in the following papers: (a) Matsumori, N.; Murata, M.; Tachibana, K. Tetrahedron 1995, 51, 12229-12238. (b) Matsumori, N.; Nonomura, T.; Sasaki, M.; Murata, M.; Tachibana, K.; Satake, M.; Yasumoto, T. Tetrahedron Lett. 1996, 37, 1269-1272. (c) Sasaki, M.; Matsumori, N.; Maruyama, T.; Nonomura, T.; Murata, M.; Tachibana, K.; Yasumoto, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1672-1675. (d) Nonomura, T.; Sasaki, M.; Matsumori, N.; Murata, M.; Tachibana, K.; Yasumoto, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1675-1678. (e) Sakai, R.; Kamiya, H.; Murata, M.; Shimamoto, K. J. Am. Chem. Soc. 1997, 119, 4112-4116. (f) Murata, M.; Matsumori, N.; Tachibana, K. Nippon Kagaku Kaishi 1997, 749-757.
21. Applications of this methodology to the configuration assignment of natural products have been published in the following papers: (a) Matsumori, N.; Murata, M.; Tachibana, K. Tetrahedron 1995, 51, 12229-12238. (b) Matsumori, N.; Nonomura, T.; Sasaki, M.; Murata, M.; Tachibana, K.; Satake, M.; Yasumoto, T. Tetrahedron Lett. 1996, 37, 1269-1272. (c) Sasaki, M.; Matsumori, N.; Maruyama, T.; Nonomura, T.; Murata, M.; Tachibana, K.; Yasumoto, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1672-1675. (d) Nonomura, T.; Sasaki, M.; Matsumori, N.; Murata, M.; Tachibana, K.; Yasumoto, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1675-1678. (e) Sakai, R.; Kamiya, H.; Murata, M.; Shimamoto, K. J. Am. Chem. Soc. 1997, 119, 4112-4116. (f) Murata, M.; Matsumori, N.; Tachibana, K. Nippon Kagaku Kaishi 1997, 749-757.
22. Applications of this methodology to the configuration assignment of natural products have been published in the following papers: (a) Matsumori, N.; Murata, M.; Tachibana, K. Tetrahedron 1995, 51, 12229-12238. (b) Matsumori, N.; Nonomura, T.; Sasaki, M.; Murata, M.; Tachibana, K.; Satake, M.; Yasumoto, T. Tetrahedron Lett. 1996, 37, 1269-1272. (c) Sasaki, M.; Matsumori, N.; Maruyama, T.; Nonomura, T.; Murata, M.; Tachibana, K.; Yasumoto, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1672-1675. (d) Nonomura, T.; Sasaki, M.; Matsumori, N.; Murata, M.; Tachibana, K.; Yasumoto, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1675-1678. (e) Sakai, R.; Kamiya, H.; Murata, M.; Shimamoto, K. J. Am. Chem. Soc. 1997, 119, 4112-4116. (f) Murata, M.; Matsumori, N.; Tachibana, K. Nippon Kagaku Kaishi 1997, 749-757.
23. Applications of this methodology to the configuration assignment of natural products have been published in the following papers: (a) Matsumori, N.; Murata, M.; Tachibana, K. Tetrahedron 1995, 51, 12229-12238. (b) Matsumori, N.; Nonomura, T.; Sasaki, M.; Murata, M.; Tachibana, K.; Satake, M.; Yasumoto, T. Tetrahedron Lett. 1996, 37, 1269-1272. (c) Sasaki, M.; Matsumori, N.; Maruyama, T.; Nonomura, T.; Murata, M.; Tachibana, K.; Yasumoto, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1672-1675. (d) Nonomura, T.; Sasaki, M.; Matsumori, N.; Murata, M.; Tachibana, K.; Yasumoto, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1675-1678. (e) Sakai, R.; Kamiya, H.; Murata, M.; Shimamoto, K. J. Am. Chem. Soc. 1997, 119, 4112-4116. (f) Murata, M.; Matsumori, N.; Tachibana, K. Nippon Kagaku Kaishi 1997, 749-757.
24. Applications of this methodology to the configuration assignment of natural products have been published in the following papers: (a) Matsumori, N.; Murata, M.; Tachibana, K. Tetrahedron 1995, 51, 12229-12238. (b) Matsumori, N.; Nonomura, T.; Sasaki, M.; Murata, M.; Tachibana, K.; Satake, M.; Yasumoto, T. Tetrahedron Lett. 1996, 37, 1269-1272. (c) Sasaki, M.; Matsumori, N.; Maruyama, T.; Nonomura, T.; Murata, M.; Tachibana, K.; Yasumoto, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1672-1675. (d) Nonomura, T.; Sasaki, M.; Matsumori, N.; Murata, M.; Tachibana, K.; Yasumoto, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1675-1678. (e) Sakai, R.; Kamiya, H.; Murata, M.; Shimamoto, K. J. Am. Chem. Soc. 1997, 119, 4112-4116. (f) Murata, M.; Matsumori, N.; Tachibana, K. Nippon Kagaku Kaishi 1997, 749-757.
25. Applications of this methodology to the configuration assignment of natural products have been published in the following papers: (a) Matsumori, N.; Murata, M.; Tachibana, K. Tetrahedron 1995, 51, 12229-12238. (b) Matsumori, N.; Nonomura, T.; Sasaki, M.; Murata, M.; Tachibana, K.; Satake, M.; Yasumoto, T. Tetrahedron Lett. 1996, 37, 1269-1272. (c) Sasaki, M.; Matsumori, N.; Maruyama, T.; Nonomura, T.; Murata, M.; Tachibana, K.; Yasumoto, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1672-1675. (d) Nonomura, T.; Sasaki, M.; Matsumori, N.; Murata, M.; Tachibana, K.; Yasumoto, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1675-1678. (e) Sakai, R.; Kamiya, H.; Murata, M.; Shimamoto, K. J. Am. Chem. Soc. 1997, 119, 4112-4116. (f) Murata, M.; Matsumori, N.; Tachibana, K. Nippon Kagaku Kaishi 1997, 749-757.
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31. C,H to conformational analyses and/or stereospecific assignments of methylene protons have been reported for proteins (a-c), carbohydrates (d, e), and polynucleotides (f, g): (a) Wang, A. C.; Bax, A. J. Am. Chem. Soc. 1996, 118, 2483-2494. (b) Kessler, H.; Griesinger, C.; Wagner, K. J. Am. Chem. Soc. 1987, 109, 6927-6933. (c) Hansen, P. E. Biochemistry 1991, 30, 10457-10466. (d) Podlasek, C. A.; Wu, J. Stripe, W. A.; Bondo, P. B.; Serianni, A. S. J. Am. Chem. Soc. 1995, 117, 8635-8644. (e) Duker, J.; Serianni, A. S. Carbohydr. Res. 1993, 249, 281-303. (f) Hines, J. V.; Landry, S. M.; Varani, G.; Tinoco, I., Jr. J. Am. Chem. Soc. 1994, 116, 5823- 5831. (g) Marino, J. P.; Schwalbe, H.; Glaser, S. J.; Griesinger, C. J. Am. Chem. Soc. 1996, 118, 4388-4395.
32. C,H to conformational analyses and/or stereospecific assignments of methylene protons have been reported for proteins (a-c), carbohydrates (d, e), and polynucleotides (f, g): (a) Wang, A. C.; Bax, A. J. Am. Chem. Soc. 1996, 118, 2483-2494. (b) Kessler, H.; Griesinger, C.; Wagner, K. J. Am. Chem. Soc. 1987, 109, 6927-6933. (c) Hansen, P. E. Biochemistry 1991, 30, 10457-10466. (d) Podlasek, C. A.; Wu, J. Stripe, W. A.; Bondo, P. B.; Serianni, A. S. J. Am. Chem. Soc. 1995, 117, 8635-8644. (e) Duker, J.; Serianni, A. S. Carbohydr. Res. 1993, 249, 281-303. (f) Hines, J. V.; Landry, S. M.; Varani, G.; Tinoco, I., Jr. J. Am. Chem. Soc. 1994, 116, 5823- 5831. (g) Marino, J. P.; Schwalbe, H.; Glaser, S. J.; Griesinger, C. J. Am. Chem. Soc. 1996, 118, 4388-4395.
33. C,H to conformational analyses and/or stereospecific assignments of methylene protons have been reported for proteins (a-c), carbohydrates (d, e), and polynucleotides (f, g): (a) Wang, A. C.; Bax, A. J. Am. Chem. Soc. 1996, 118, 2483-2494. (b) Kessler, H.; Griesinger, C.; Wagner, K. J. Am. Chem. Soc. 1987, 109, 6927-6933. (c) Hansen, P. E. Biochemistry 1991, 30, 10457-10466. (d) Podlasek, C. A.; Wu, J. Stripe, W. A.; Bondo, P. B.; Serianni, A. S. J. Am. Chem. Soc. 1995, 117, 8635-8644. (e) Duker, J.; Serianni, A. S. Carbohydr. Res. 1993, 249, 281-303. (f) Hines, J. V.; Landry, S. M.; Varani, G.; Tinoco, I., Jr. J. Am. Chem. Soc. 1994, 116, 5823- 5831. (g) Marino, J. P.; Schwalbe, H.; Glaser, S. J.; Griesinger, C. J. Am. Chem. Soc. 1996, 118, 4388-4395.
34. C,H to conformational analyses and/or stereospecific assignments of methylene protons have been reported for proteins (a-c), carbohydrates (d, e), and polynucleotides (f, g): (a) Wang, A. C.; Bax, A. J. Am. Chem. Soc. 1996, 118, 2483-2494. (b) Kessler, H.; Griesinger, C.; Wagner, K. J. Am. Chem. Soc. 1987, 109, 6927-6933. (c) Hansen, P. E. Biochemistry 1991, 30, 10457-10466. (d) Podlasek, C. A.; Wu, J. Stripe, W. A.; Bondo, P. B.; Serianni, A. S. J. Am. Chem. Soc. 1995, 117, 8635-8644. (e) Duker, J.; Serianni, A. S. Carbohydr. Res. 1993, 249, 281-303. (f) Hines, J. V.; Landry, S. M.; Varani, G.; Tinoco, I., Jr. J. Am. Chem. Soc. 1994, 116, 5823- 5831. (g) Marino, J. P.; Schwalbe, H.; Glaser, S. J.; Griesinger, C. J. Am. Chem. Soc. 1996, 118, 4388-4395.
35. C,H to conformational analyses and/or stereospecific assignments of methylene protons have been reported for proteins (a-c), carbohydrates (d, e), and polynucleotides (f, g): (a) Wang, A. C.; Bax, A. J. Am. Chem. Soc. 1996, 118, 2483-2494. (b) Kessler, H.; Griesinger, C.; Wagner, K. J. Am. Chem. Soc. 1987, 109, 6927-6933. (c) Hansen, P. E. Biochemistry 1991, 30, 10457-10466. (d) Podlasek, C. A.; Wu, J. Stripe, W. A.; Bondo, P. B.; Serianni, A. S. J. Am. Chem. Soc. 1995, 117, 8635-8644. (e) Duker, J.; Serianni, A. S. Carbohydr. Res. 1993, 249, 281-303. (f) Hines, J. V.; Landry, S. M.; Varani, G.; Tinoco, I., Jr. J. Am. Chem. Soc. 1994, 116, 5823-5831. (g) Marino, J. P.; Schwalbe, H.; Glaser, S. J.; Griesinger, C. J. Am. Chem. Soc. 1996, 118, 4388-4395.
36. C,H to conformational analyses and/or stereospecific assignments of methylene protons have been reported for proteins (a-c), carbohydrates (d, e), and polynucleotides (f, g): (a) Wang, A. C.; Bax, A. J. Am. Chem. Soc. 1996, 118, 2483-2494. (b) Kessler, H.; Griesinger, C.; Wagner, K. J. Am. Chem. Soc. 1987, 109, 6927-6933. (c) Hansen, P. E. Biochemistry 1991, 30, 10457-10466. (d) Podlasek, C. A.; Wu, J. Stripe, W. A.; Bondo, P. B.; Serianni, A. S. J. Am. Chem. Soc. 1995, 117, 8635-8644. (e) Duker, J.; Serianni, A. S. Carbohydr. Res. 1993, 249, 281-303. (f) Hines, J. V.; Landry, S. M.; Varani, G.; Tinoco, I., Jr. J. Am. Chem. Soc. 1994, 116, 5823- 5831. (g) Marino, J. P.; Schwalbe, H.; Glaser, S. J.; Griesinger, C. J. Am. Chem. Soc. 1996, 118, 4388-4395.
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40. 13c,d To such systems, the J-based method was successfully applied. Although applications to acyloxy substitutions are not plentiful, preliminary investigations on tri-O-acetyl model compounds 1 and 2 suggested that this method can be applied for acetoxy-substituted chains.
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49. 22
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51. 6 sometimes show prominent NOEs from OH protons in these systems. NOE range (equation presented) A-3 B-3
52. C,H (Figure 5). A minor conformer with 10% or less population does not affect the average J value significantly, and thus its presence does not usually result in a deviation in J values.
53. 3.
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55. As judged from their relaxation times, molecular motions and internal rotations of 1-4 seemed to be much faster than those of natural products with masses around 1000 Da, for which this J-based method was originally designed. Measurements at low temperature, which slow these motions to the level of larger molecules, resulted in decreasing the population of the minor conformers in 1-4. The values at low temperature in parentheses (Table 3) may reproduce the corresponding stucture units in larger molecules more precisely.
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58. Nakamura, H.; Maruyama, K.; Murai, A. Abstracts of Papers, 72th Annual Meeting of Japan Society of Chemistry, Tokyo; Japan Society of Chemistry: Tokyo, 1997; 3G4 29 (p 1048). Structural studies by synthesis will be published elsewhere.
59. The relative configuration of side chains of maitotoxin has been independently elucidated by Harvard group, who reached the identical conclusion: Zheng, W.; DeMattei, J. A.; Wu, J.-P.; Duan, J. J.-W.; Cook, L. R.; Oinuma, H.; Kishi, Y. J. Am. Chem. Soc. 1996, 118, 7946-7968.
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61. (a) Griesinger, C.; Sørensen, O. W.; Ernst, R. R. J. Am. Chem. Soc. 1985, 107, 6394-6396. P.E. COSY (Mueller, L. J. Magn. Reson. 1987, 72, 191-196) could be used in lieu of E. COSY.
62. (a) Griesinger, C.; Sørensen, O. W.; Ernst, R. R. J. Am. Chem. Soc. 1985, 107, 6394-6396. P.E. COSY (Mueller, L. J. Magn. Reson. 1987, 72, 191-196) could be used in lieu of E. COSY.