8-Endo cyclization of (alkoxycarbonyl)methyl radicals: Radical ways for preparation of eight-membered-ring lactones

Journal of the American Chemical Society

Volumn 120, Issue 30, 1998, Pages 7469-7478

  Lee, Eun ^a   Yoon, Cheol Hwan ^a   Lee, Tae Hee ^a   Kim, Sun Young ^a   Ha, Tae Joon ^a   Sung, Yong Suk ^a   Park, Sang Hyun ^a   Lee, Sangyoub ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE DERIVATIVE;

ARTICLE; CALCULATION; CHIRALITY; CYCLIZATION; DRUG SYNTHESIS; IN VITRO STUDY; MASS SPECTROMETRY; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY; THEORY; THIN LAYER CHROMATOGRAPHY;

EID: 0032486763     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja980908d     Document Type: Article

References (86)

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21. The difficulty in the formation of heptanolactones is discussed in the following examples: (a) Mukaiyama, T.; Usui, M.; Saigo, K. Chem. Lett. 1976, 49. (b) Galli, C.; Illuminati, G.; Mandolini, L. J. Am. Chem. Soc. 1973, 95, 8374. (c) Galli, C.; Illuminati, G.; Mandolini, L.; Tamborra, P. J. Am. Chem. Soc. 1977, 99, 2591. (d) Galli, C.; Mandolini, L. J. Chem. Soc., Chem. Commun. 1982, 251. (e) Simonot, B.; Rousseau, G. J. Org. Chem. 1994, 59, 5912.
22. The difficulty in the formation of heptanolactones is discussed in the following examples: (a) Mukaiyama, T.; Usui, M.; Saigo, K. Chem. Lett. 1976, 49. (b) Galli, C.; Illuminati, G.; Mandolini, L. J. Am. Chem. Soc. 1973, 95, 8374. (c) Galli, C.; Illuminati, G.; Mandolini, L.; Tamborra, P. J. Am. Chem. Soc. 1977, 99, 2591. (d) Galli, C.; Mandolini, L. J. Chem. Soc., Chem. Commun. 1982, 251. (e) Simonot, B.; Rousseau, G. J. Org. Chem. 1994, 59, 5912.
23. The difficulty in the formation of heptanolactones is discussed in the following examples: (a) Mukaiyama, T.; Usui, M.; Saigo, K. Chem. Lett. 1976, 49. (b) Galli, C.; Illuminati, G.; Mandolini, L. J. Am. Chem. Soc. 1973, 95, 8374. (c) Galli, C.; Illuminati, G.; Mandolini, L.; Tamborra, P. J. Am. Chem. Soc. 1977, 99, 2591. (d) Galli, C.; Mandolini, L. J. Chem. Soc., Chem. Commun. 1982, 251. (e) Simonot, B.; Rousseau, G. J. Org. Chem. 1994, 59, 5912.
24. The difficulty in the formation of heptanolactones is discussed in the following examples: (a) Mukaiyama, T.; Usui, M.; Saigo, K. Chem. Lett. 1976, 49. (b) Galli, C.; Illuminati, G.; Mandolini, L. J. Am. Chem. Soc. 1973, 95, 8374. (c) Galli, C.; Illuminati, G.; Mandolini, L.; Tamborra, P. J. Am. Chem. Soc. 1977, 99, 2591. (d) Galli, C.; Mandolini, L. J. Chem. Soc., Chem. Commun. 1982, 251. (e) Simonot, B.; Rousseau, G. J. Org. Chem. 1994, 59, 5912.
25. In many other examples, heptanolactones are omitted as targets but it is obvious that they are the most difficult ones: (a) Corey, E. J.; Nicolaou, K. C. J. Am. Chem. Soc. 1974, 96, 5614. (b) Kurihara, T.; Nakajima, Y.; Mitsunobu, O. Tetrahedron Lett. 1976, 2455. (c) Vorbrüggen, H.; Krolikiewicz, K. Angew. Chem., Int. Ed. Engl. 1977, 16, 876. (d) Kruizinga, W. H.; Kellogg, R. M. J. Chem. Soc., Chem. Commun. 1979, 286. (e) Steliou, K.; Szczygielska-Nowosielska, A.; Favre, A.; Poupart, M. A.; Hanessian, S. J. Am. Chem. Soc. 1980, 102, 7578. (f) Kruizinga, W. H.; Kellogg, R. M. J. Am. Chem. Soc. 1981, 103, 5183. (g) Regen, S. L.; Kimura, Y. J. Am. Chem. Soc. 1982, 104, 2064. (h) Steliou, K.; Poupart, M. A. J. Am. Chem. Soc. 1983, 105, 7130. (i) Kimura, Y.; Regen, S. L. J. Org. Chem. 1983, 48, 1533.
26. In many other examples, heptanolactones are omitted as targets but it is obvious that they are the most difficult ones: (a) Corey, E. J.; Nicolaou, K. C. J. Am. Chem. Soc. 1974, 96, 5614. (b) Kurihara, T.; Nakajima, Y.; Mitsunobu, O. Tetrahedron Lett. 1976, 2455. (c) Vorbrüggen, H.; Krolikiewicz, K. Angew. Chem., Int. Ed. Engl. 1977, 16, 876. (d) Kruizinga, W. H.; Kellogg, R. M. J. Chem. Soc., Chem. Commun. 1979, 286. (e) Steliou, K.; Szczygielska-Nowosielska, A.; Favre, A.; Poupart, M. A.; Hanessian, S. J. Am. Chem. Soc. 1980, 102, 7578. (f) Kruizinga, W. H.; Kellogg, R. M. J. Am. Chem. Soc. 1981, 103, 5183. (g) Regen, S. L.; Kimura, Y. J. Am. Chem. Soc. 1982, 104, 2064. (h) Steliou, K.; Poupart, M. A. J. Am. Chem. Soc. 1983, 105, 7130. (i) Kimura, Y.; Regen, S. L. J. Org. Chem. 1983, 48, 1533.
27. In many other examples, heptanolactones are omitted as targets but it is obvious that they are the most difficult ones: (a) Corey, E. J.; Nicolaou, K. C. J. Am. Chem. Soc. 1974, 96, 5614. (b) Kurihara, T.; Nakajima, Y.; Mitsunobu, O. Tetrahedron Lett. 1976, 2455. (c) Vorbrüggen, H.; Krolikiewicz, K. Angew. Chem., Int. Ed. Engl. 1977, 16, 876. (d) Kruizinga, W. H.; Kellogg, R. M. J. Chem. Soc., Chem. Commun. 1979, 286. (e) Steliou, K.; Szczygielska-Nowosielska, A.; Favre, A.; Poupart, M. A.; Hanessian, S. J. Am. Chem. Soc. 1980, 102, 7578. (f) Kruizinga, W. H.; Kellogg, R. M. J. Am. Chem. Soc. 1981, 103, 5183. (g) Regen, S. L.; Kimura, Y. J. Am. Chem. Soc. 1982, 104, 2064. (h) Steliou, K.; Poupart, M. A. J. Am. Chem. Soc. 1983, 105, 7130. (i) Kimura, Y.; Regen, S. L. J. Org. Chem. 1983, 48, 1533.
28. In many other examples, heptanolactones are omitted as targets but it is obvious that they are the most difficult ones: (a) Corey, E. J.; Nicolaou, K. C. J. Am. Chem. Soc. 1974, 96, 5614. (b) Kurihara, T.; Nakajima, Y.; Mitsunobu, O. Tetrahedron Lett. 1976, 2455. (c) Vorbrüggen, H.; Krolikiewicz, K. Angew. Chem., Int. Ed. Engl. 1977, 16, 876. (d) Kruizinga, W. H.; Kellogg, R. M. J. Chem. Soc., Chem. Commun. 1979, 286. (e) Steliou, K.; Szczygielska-Nowosielska, A.; Favre, A.; Poupart, M. A.; Hanessian, S. J. Am. Chem. Soc. 1980, 102, 7578. (f) Kruizinga, W. H.; Kellogg, R. M. J. Am. Chem. Soc. 1981, 103, 5183. (g) Regen, S. L.; Kimura, Y. J. Am. Chem. Soc. 1982, 104, 2064. (h) Steliou, K.; Poupart, M. A. J. Am. Chem. Soc. 1983, 105, 7130. (i) Kimura, Y.; Regen, S. L. J. Org. Chem. 1983, 48, 1533.
29. In many other examples, heptanolactones are omitted as targets but it is obvious that they are the most difficult ones: (a) Corey, E. J.; Nicolaou, K. C. J. Am. Chem. Soc. 1974, 96, 5614. (b) Kurihara, T.; Nakajima, Y.; Mitsunobu, O. Tetrahedron Lett. 1976, 2455. (c) Vorbrüggen, H.; Krolikiewicz, K. Angew. Chem., Int. Ed. Engl. 1977, 16, 876. (d) Kruizinga, W. H.; Kellogg, R. M. J. Chem. Soc., Chem. Commun. 1979, 286. (e) Steliou, K.; Szczygielska-Nowosielska, A.; Favre, A.; Poupart, M. A.; Hanessian, S. J. Am. Chem. Soc. 1980, 102, 7578. (f) Kruizinga, W. H.; Kellogg, R. M. J. Am. Chem. Soc. 1981, 103, 5183. (g) Regen, S. L.; Kimura, Y. J. Am. Chem. Soc. 1982, 104, 2064. (h) Steliou, K.; Poupart, M. A. J. Am. Chem. Soc. 1983, 105, 7130. (i) Kimura, Y.; Regen, S. L. J. Org. Chem. 1983, 48, 1533.
30. In many other examples, heptanolactones are omitted as targets but it is obvious that they are the most difficult ones: (a) Corey, E. J.; Nicolaou, K. C. J. Am. Chem. Soc. 1974, 96, 5614. (b) Kurihara, T.; Nakajima, Y.; Mitsunobu, O. Tetrahedron Lett. 1976, 2455. (c) Vorbrüggen, H.; Krolikiewicz, K. Angew. Chem., Int. Ed. Engl. 1977, 16, 876. (d) Kruizinga, W. H.; Kellogg, R. M. J. Chem. Soc., Chem. Commun. 1979, 286. (e) Steliou, K.; Szczygielska-Nowosielska, A.; Favre, A.; Poupart, M. A.; Hanessian, S. J. Am. Chem. Soc. 1980, 102, 7578. (f) Kruizinga, W. H.; Kellogg, R. M. J. Am. Chem. Soc. 1981, 103, 5183. (g) Regen, S. L.; Kimura, Y. J. Am. Chem. Soc. 1982, 104, 2064. (h) Steliou, K.; Poupart, M. A. J. Am. Chem. Soc. 1983, 105, 7130. (i) Kimura, Y.; Regen, S. L. J. Org. Chem. 1983, 48, 1533.
31. In many other examples, heptanolactones are omitted as targets but it is obvious that they are the most difficult ones: (a) Corey, E. J.; Nicolaou, K. C. J. Am. Chem. Soc. 1974, 96, 5614. (b) Kurihara, T.; Nakajima, Y.; Mitsunobu, O. Tetrahedron Lett. 1976, 2455. (c) Vorbrüggen, H.; Krolikiewicz, K. Angew. Chem., Int. Ed. Engl. 1977, 16, 876. (d) Kruizinga, W. H.; Kellogg, R. M. J. Chem. Soc., Chem. Commun. 1979, 286. (e) Steliou, K.; Szczygielska-Nowosielska, A.; Favre, A.; Poupart, M. A.; Hanessian, S. J. Am. Chem. Soc. 1980, 102, 7578. (f) Kruizinga, W. H.; Kellogg, R. M. J. Am. Chem. Soc. 1981, 103, 5183. (g) Regen, S. L.; Kimura, Y. J. Am. Chem. Soc. 1982, 104, 2064. (h) Steliou, K.; Poupart, M. A. J. Am. Chem. Soc. 1983, 105, 7130. (i) Kimura, Y.; Regen, S. L. J. Org. Chem. 1983, 48, 1533.
32. In many other examples, heptanolactones are omitted as targets but it is obvious that they are the most difficult ones: (a) Corey, E. J.; Nicolaou, K. C. J. Am. Chem. Soc. 1974, 96, 5614. (b) Kurihara, T.; Nakajima, Y.; Mitsunobu, O. Tetrahedron Lett. 1976, 2455. (c) Vorbrüggen, H.; Krolikiewicz, K. Angew. Chem., Int. Ed. Engl. 1977, 16, 876. (d) Kruizinga, W. H.; Kellogg, R. M. J. Chem. Soc., Chem. Commun. 1979, 286. (e) Steliou, K.; Szczygielska-Nowosielska, A.; Favre, A.; Poupart, M. A.; Hanessian, S. J. Am. Chem. Soc. 1980, 102, 7578. (f) Kruizinga, W. H.; Kellogg, R. M. J. Am. Chem. Soc. 1981, 103, 5183. (g) Regen, S. L.; Kimura, Y. J. Am. Chem. Soc. 1982, 104, 2064. (h) Steliou, K.; Poupart, M. A. J. Am. Chem. Soc. 1983, 105, 7130. (i) Kimura, Y.; Regen, S. L. J. Org. Chem. 1983, 48, 1533.
33. In many other examples, heptanolactones are omitted as targets but it is obvious that they are the most difficult ones: (a) Corey, E. J.; Nicolaou, K. C. J. Am. Chem. Soc. 1974, 96, 5614. (b) Kurihara, T.; Nakajima, Y.; Mitsunobu, O. Tetrahedron Lett. 1976, 2455. (c) Vorbrüggen, H.; Krolikiewicz, K. Angew. Chem., Int. Ed. Engl. 1977, 16, 876. (d) Kruizinga, W. H.; Kellogg, R. M. J. Chem. Soc., Chem. Commun. 1979, 286. (e) Steliou, K.; Szczygielska-Nowosielska, A.; Favre, A.; Poupart, M. A.; Hanessian, S. J. Am. Chem. Soc. 1980, 102, 7578. (f) Kruizinga, W. H.; Kellogg, R. M. J. Am. Chem. Soc. 1981, 103, 5183. (g) Regen, S. L.; Kimura, Y. J. Am. Chem. Soc. 1982, 104, 2064. (h) Steliou, K.; Poupart, M. A. J. Am. Chem. Soc. 1983, 105, 7130. (i) Kimura, Y.; Regen, S. L. J. Org. Chem. 1983, 48, 1533.
34. There are a few recent examples of successful formation of heptanolactones from substituted 7-hydroxyheptanoic acids. In these cases, the conformational constraint imposed by the substituents is considered important: (a) Funk, R. L.; Abelman, M. M. J. Org. Chem. 1986, 51, 3247. (b) Buszek, K. R.; Sato, N.; Jeong, Y. J. Am. Chem. Soc. 1994, 116, 5511. (c) Andrus, M. B.; Argade, A. B. Tetrahedron Lett. 1996, 37, 5049.
35. There are a few recent examples of successful formation of heptanolactones from substituted 7-hydroxyheptanoic acids. In these cases, the conformational constraint imposed by the substituents is considered important: (a) Funk, R. L.; Abelman, M. M. J. Org. Chem. 1986, 51, 3247. (b) Buszek, K. R.; Sato, N.; Jeong, Y. J. Am. Chem. Soc. 1994, 116, 5511. (c) Andrus, M. B.; Argade, A. B. Tetrahedron Lett. 1996, 37, 5049.
36. There are a few recent examples of successful formation of heptanolactones from substituted 7-hydroxyheptanoic acids. In these cases, the conformational constraint imposed by the substituents is considered important: (a) Funk, R. L.; Abelman, M. M. J. Org. Chem. 1986, 51, 3247. (b) Buszek, K. R.; Sato, N.; Jeong, Y. J. Am. Chem. Soc. 1994, 116, 5511. (c) Andrus, M. B.; Argade, A. B. Tetrahedron Lett. 1996, 37, 5049.
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