Total synthesis of (-)-verrucarol

Journal of Organic Chemistry

Volumn 63, Issue 8, 1998, Pages 2679-2688

  Ishihara, Jun ^a,b   Nonaka, Rie ^a   Terasawa, Yuki ^a   Shiraki, Ryota ^a   Yabu, Kazuo ^a   Kataoka, Hiromi ^a   Ochiai, Yuichi ^a   Tadano, Kin Ichi ^a  

^a KEIO UNIVERSITY   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CALONECTIN; DIACETOXYSCIRPENOL; SESQUITERPENOID; TRICHODERMIN; TRICHODERMOL; TRICHODIENE; TRICHOTHECIN; UNCLASSIFIED DRUG; VERRUCARIN A; VERRUCAROL DERIVATIVE;

ARTICLE; CYCLIZATION; DECARBOXYLATION; DRUG SYNTHESIS; ENANTIOMER; PROTEIN QUATERNARY STRUCTURE; STEREOCHEMISTRY;

EID: 0032540434     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo972309f     Document Type: Article

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61. Some representative articles on this subject: (a) Welch, S. C.; Wong, R. Y. Tetrahedron Lett. 1972, 1855. (b) Yamakawa, K.; Kurita, J.; Sakaguchi, R. Tetrahedron Lett. 1973, 3877. Goldsmith, D. J.; Lewis, A. J.; Still, W. C., Jr. Tetrahedron Lett. 1973, 4807. Masuoka, N.; Kamikawa, T.; Kubota, T. Chem. Lett. 1974, 751. (e) Fujimoto, Y.; Yokura, S.; Nakamura, T.; Morikawa, T.; Tatsuno, T. Tetrahedron Lett. 1974, 2523. (f) Masuoka, N.; Kamikawa, T. Tetrahedron Lett. 1976, 1691. (g) Yamakawa, K.; Sakaguchi, R.; Nakamura, T.; Watanabe, K. Chem. Lett. 1976, 991. (h) Colvin, E. W.; Malchenko, S.; Raphael, R. A.; Roberts, J. S. J. Chem. Soc., Perkin Trans. 1, 1978, 658. Nakahara, Y.; Tatsuno, T. Chem. Pharm. Bull. 1980, 28, 1981. (j) Goldsmith, D. J.; John, T. K.; Kwong, C. D.; Painter, G. R. J. Org. Chem. 1980, 45, 3989. (k) Kraus, G. A.; Frazier, K. J. Org. Chem. 1980, 45, 4820. Kraus, G. A.; Roth, B. J. Org. Chem. 1980, 45, 4825. (n) White, J. D.; Matsui, T.; Thomas, J. A. J. Org. Chem. 1981, 46, 3376. (o) Pearson, A. J.; Ong, C. W. J. Am. Chem. Soc. 1981, 103, 6686. (p) Ziegler, F. E.; Nangia, A.; Schulte, G. J. Am. Chem. Soc. 1987, 109, 3987. (q) Colvin, E. W.; Egan, M. J.; Kerr, F. W. J. Chem. Soc., Chem. Commun. 1990, 1200. (r) Ziegler, F. E.; Sobolov, S. B. J. Am. Chem. Soc. 1990, 112, 2749. (s) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1996, 42, 165. (t) Nemoto, H.; Miyata, J. Fukumoto, K. Tetrahedron, 1996, 52, 10363. (u) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1997, 44, 125.
62. Some representative articles on this subject: (a) Welch, S. C.; Wong, R. Y. Tetrahedron Lett. 1972, 1855. (b) Yamakawa, K.; Kurita, J.; Sakaguchi, R. Tetrahedron Lett. 1973, 3877. Goldsmith, D. J.; Lewis, A. J.; Still, W. C., Jr. Tetrahedron Lett. 1973, 4807. Masuoka, N.; Kamikawa, T.; Kubota, T. Chem. Lett. 1974, 751. (e) Fujimoto, Y.; Yokura, S.; Nakamura, T.; Morikawa, T.; Tatsuno, T. Tetrahedron Lett. 1974, 2523. (f) Masuoka, N.; Kamikawa, T. Tetrahedron Lett. 1976, 1691. (g) Yamakawa, K.; Sakaguchi, R.; Nakamura, T.; Watanabe, K. Chem. Lett. 1976, 991. (h) Colvin, E. W.; Malchenko, S.; Raphael, R. A.; Roberts, J. S. J. Chem. Soc., Perkin Trans. 1, 1978, 658. Nakahara, Y.; Tatsuno, T. Chem. Pharm. Bull. 1980, 28, 1981. (j) Goldsmith, D. J.; John, T. K.; Kwong, C. D.; Painter, G. R. J. Org. Chem. 1980, 45, 3989. (k) Kraus, G. A.; Frazier, K. J. Org. Chem. 1980, 45, 4820. Kraus, G. A.; Roth, B. J. Org. Chem. 1980, 45, 4825. (n) White, J. D.; Matsui, T.; Thomas, J. A. J. Org. Chem. 1981, 46, 3376. (o) Pearson, A. J.; Ong, C. W. J. Am. Chem. Soc. 1981, 103, 6686. (p) Ziegler, F. E.; Nangia, A.; Schulte, G. J. Am. Chem. Soc. 1987, 109, 3987. (q) Colvin, E. W.; Egan, M. J.; Kerr, F. W. J. Chem. Soc., Chem. Commun. 1990, 1200. (r) Ziegler, F. E.; Sobolov, S. B. J. Am. Chem. Soc. 1990, 112, 2749. (s) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1996, 42, 165. (t) Nemoto, H.; Miyata, J. Fukumoto, K. Tetrahedron, 1996, 52, 10363. (u) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1997, 44, 125.
63. Some representative articles on this subject: (a) Welch, S. C.; Wong, R. Y. Tetrahedron Lett. 1972, 1855. (b) Yamakawa, K.; Kurita, J.; Sakaguchi, R. Tetrahedron Lett. 1973, 3877. Goldsmith, D. J.; Lewis, A. J.; Still, W. C., Jr. Tetrahedron Lett. 1973, 4807. Masuoka, N.; Kamikawa, T.; Kubota, T. Chem. Lett. 1974, 751. (e) Fujimoto, Y.; Yokura, S.; Nakamura, T.; Morikawa, T.; Tatsuno, T. Tetrahedron Lett. 1974, 2523. (f) Masuoka, N.; Kamikawa, T. Tetrahedron Lett. 1976, 1691. (g) Yamakawa, K.; Sakaguchi, R.; Nakamura, T.; Watanabe, K. Chem. Lett. 1976, 991. (h) Colvin, E. W.; Malchenko, S.; Raphael, R. A.; Roberts, J. S. J. Chem. Soc., Perkin Trans. 1, 1978, 658. Nakahara, Y.; Tatsuno, T. Chem. Pharm. Bull. 1980, 28, 1981. (j) Goldsmith, D. J.; John, T. K.; Kwong, C. D.; Painter, G. R. J. Org. Chem. 1980, 45, 3989. (k) Kraus, G. A.; Frazier, K. J. Org. Chem. 1980, 45, 4820. Kraus, G. A.; Roth, B. J. Org. Chem. 1980, 45, 4825. (n) White, J. D.; Matsui, T.; Thomas, J. A. J. Org. Chem. 1981, 46, 3376. (o) Pearson, A. J.; Ong, C. W. J. Am. Chem. Soc. 1981, 103, 6686. (p) Ziegler, F. E.; Nangia, A.; Schulte, G. J. Am. Chem. Soc. 1987, 109, 3987. (q) Colvin, E. W.; Egan, M. J.; Kerr, F. W. J. Chem. Soc., Chem. Commun. 1990, 1200. (r) Ziegler, F. E.; Sobolov, S. B. J. Am. Chem. Soc. 1990, 112, 2749. (s) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1996, 42, 165. (t) Nemoto, H.; Miyata, J. Fukumoto, K. Tetrahedron, 1996, 52, 10363. (u) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1997, 44, 125.
64. Some representative articles on this subject: (a) Welch, S. C.; Wong, R. Y. Tetrahedron Lett. 1972, 1855. (b) Yamakawa, K.; Kurita, J.; Sakaguchi, R. Tetrahedron Lett. 1973, 3877. Goldsmith, D. J.; Lewis, A. J.; Still, W. C., Jr. Tetrahedron Lett. 1973, 4807. Masuoka, N.; Kamikawa, T.; Kubota, T. Chem. Lett. 1974, 751. (e) Fujimoto, Y.; Yokura, S.; Nakamura, T.; Morikawa, T.; Tatsuno, T. Tetrahedron Lett. 1974, 2523. (f) Masuoka, N.; Kamikawa, T. Tetrahedron Lett. 1976, 1691. (g) Yamakawa, K.; Sakaguchi, R.; Nakamura, T.; Watanabe, K. Chem. Lett. 1976, 991. (h) Colvin, E. W.; Malchenko, S.; Raphael, R. A.; Roberts, J. S. J. Chem. Soc., Perkin Trans. 1, 1978, 658. Nakahara, Y.; Tatsuno, T. Chem. Pharm. Bull. 1980, 28, 1981. (j) Goldsmith, D. J.; John, T. K.; Kwong, C. D.; Painter, G. R. J. Org. Chem. 1980, 45, 3989. (k) Kraus, G. A.; Frazier, K. J. Org. Chem. 1980, 45, 4820. Kraus, G. A.; Roth, B. J. Org. Chem. 1980, 45, 4825. (n) White, J. D.; Matsui, T.; Thomas, J. A. J. Org. Chem. 1981, 46, 3376. (o) Pearson, A. J.; Ong, C. W. J. Am. Chem. Soc. 1981, 103, 6686. (p) Ziegler, F. E.; Nangia, A.; Schulte, G. J. Am. Chem. Soc. 1987, 109, 3987. (q) Colvin, E. W.; Egan, M. J.; Kerr, F. W. J. Chem. Soc., Chem. Commun. 1990, 1200. (r) Ziegler, F. E.; Sobolov, S. B. J. Am. Chem. Soc. 1990, 112, 2749. (s) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1996, 42, 165. (t) Nemoto, H.; Miyata, J. Fukumoto, K. Tetrahedron, 1996, 52, 10363. (u) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1997, 44, 125.
65. Some representative articles on this subject: (a) Welch, S. C.; Wong, R. Y. Tetrahedron Lett. 1972, 1855. (b) Yamakawa, K.; Kurita, J.; Sakaguchi, R. Tetrahedron Lett. 1973, 3877. Goldsmith, D. J.; Lewis, A. J.; Still, W. C., Jr. Tetrahedron Lett. 1973, 4807. Masuoka, N.; Kamikawa, T.; Kubota, T. Chem. Lett. 1974, 751. (e) Fujimoto, Y.; Yokura, S.; Nakamura, T.; Morikawa, T.; Tatsuno, T. Tetrahedron Lett. 1974, 2523. (f) Masuoka, N.; Kamikawa, T. Tetrahedron Lett. 1976, 1691. (g) Yamakawa, K.; Sakaguchi, R.; Nakamura, T.; Watanabe, K. Chem. Lett. 1976, 991. (h) Colvin, E. W.; Malchenko, S.; Raphael, R. A.; Roberts, J. S. J. Chem. Soc., Perkin Trans. 1, 1978, 658. Nakahara, Y.; Tatsuno, T. Chem. Pharm. Bull. 1980, 28, 1981. (j) Goldsmith, D. J.; John, T. K.; Kwong, C. D.; Painter, G. R. J. Org. Chem. 1980, 45, 3989. (k) Kraus, G. A.; Frazier, K. J. Org. Chem. 1980, 45, 4820. Kraus, G. A.; Roth, B. J. Org. Chem. 1980, 45, 4825. (n) White, J. D.; Matsui, T.; Thomas, J. A. J. Org. Chem. 1981, 46, 3376. (o) Pearson, A. J.; Ong, C. W. J. Am. Chem. Soc. 1981, 103, 6686. (p) Ziegler, F. E.; Nangia, A.; Schulte, G. J. Am. Chem. Soc. 1987, 109, 3987. (q) Colvin, E. W.; Egan, M. J.; Kerr, F. W. J. Chem. Soc., Chem. Commun. 1990, 1200. (r) Ziegler, F. E.; Sobolov, S. B. J. Am. Chem. Soc. 1990, 112, 2749. (s) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1996, 42, 165. (t) Nemoto, H.; Miyata, J. Fukumoto, K. Tetrahedron, 1996, 52, 10363. (u) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1997, 44, 125.
66. Some representative articles on this subject: (a) Welch, S. C.; Wong, R. Y. Tetrahedron Lett. 1972, 1855. (b) Yamakawa, K.; Kurita, J.; Sakaguchi, R. Tetrahedron Lett. 1973, 3877. Goldsmith, D. J.; Lewis, A. J.; Still, W. C., Jr. Tetrahedron Lett. 1973, 4807. Masuoka, N.; Kamikawa, T.; Kubota, T. Chem. Lett. 1974, 751. (e) Fujimoto, Y.; Yokura, S.; Nakamura, T.; Morikawa, T.; Tatsuno, T. Tetrahedron Lett. 1974, 2523. (f) Masuoka, N.; Kamikawa, T. Tetrahedron Lett. 1976, 1691. (g) Yamakawa, K.; Sakaguchi, R.; Nakamura, T.; Watanabe, K. Chem. Lett. 1976, 991. (h) Colvin, E. W.; Malchenko, S.; Raphael, R. A.; Roberts, J. S. J. Chem. Soc., Perkin Trans. 1, 1978, 658. Nakahara, Y.; Tatsuno, T. Chem. Pharm. Bull. 1980, 28, 1981. (j) Goldsmith, D. J.; John, T. K.; Kwong, C. D.; Painter, G. R. J. Org. Chem. 1980, 45, 3989. (k) Kraus, G. A.; Frazier, K. J. Org. Chem. 1980, 45, 4820. Kraus, G. A.; Roth, B. J. Org. Chem. 1980, 45, 4825. (n) White, J. D.; Matsui, T.; Thomas, J. A. J. Org. Chem. 1981, 46, 3376. (o) Pearson, A. J.; Ong, C. W. J. Am. Chem. Soc. 1981, 103, 6686. (p) Ziegler, F. E.; Nangia, A.; Schulte, G. J. Am. Chem. Soc. 1987, 109, 3987. (q) Colvin, E. W.; Egan, M. J.; Kerr, F. W. J. Chem. Soc., Chem. Commun. 1990, 1200. (r) Ziegler, F. E.; Sobolov, S. B. J. Am. Chem. Soc. 1990, 112, 2749. (s) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1996, 42, 165. (t) Nemoto, H.; Miyata, J. Fukumoto, K. Tetrahedron, 1996, 52, 10363. (u) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1997, 44, 125.
67. Some representative articles on this subject: (a) Welch, S. C.; Wong, R. Y. Tetrahedron Lett. 1972, 1855. (b) Yamakawa, K.; Kurita, J.; Sakaguchi, R. Tetrahedron Lett. 1973, 3877. Goldsmith, D. J.; Lewis, A. J.; Still, W. C., Jr. Tetrahedron Lett. 1973, 4807. Masuoka, N.; Kamikawa, T.; Kubota, T. Chem. Lett. 1974, 751. (e) Fujimoto, Y.; Yokura, S.; Nakamura, T.; Morikawa, T.; Tatsuno, T. Tetrahedron Lett. 1974, 2523. (f) Masuoka, N.; Kamikawa, T. Tetrahedron Lett. 1976, 1691. (g) Yamakawa, K.; Sakaguchi, R.; Nakamura, T.; Watanabe, K. Chem. Lett. 1976, 991. (h) Colvin, E. W.; Malchenko, S.; Raphael, R. A.; Roberts, J. S. J. Chem. Soc., Perkin Trans. 1, 1978, 658. Nakahara, Y.; Tatsuno, T. Chem. Pharm. Bull. 1980, 28, 1981. (j) Goldsmith, D. J.; John, T. K.; Kwong, C. D.; Painter, G. R. J. Org. Chem. 1980, 45, 3989. (k) Kraus, G. A.; Frazier, K. J. Org. Chem. 1980, 45, 4820. Kraus, G. A.; Roth, B. J. Org. Chem. 1980, 45, 4825. (n) White, J. D.; Matsui, T.; Thomas, J. A. J. Org. Chem. 1981, 46, 3376. (o) Pearson, A. J.; Ong, C. W. J. Am. Chem. Soc. 1981, 103, 6686. (p) Ziegler, F. E.; Nangia, A.; Schulte, G. J. Am. Chem. Soc. 1987, 109, 3987. (q) Colvin, E. W.; Egan, M. J.; Kerr, F. W. J. Chem. Soc., Chem. Commun. 1990, 1200. (r) Ziegler, F. E.; Sobolov, S. B. J. Am. Chem. Soc. 1990, 112, 2749. (s) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1996, 42, 165. (t) Nemoto, H.; Miyata, J. Fukumoto, K. Tetrahedron, 1996, 52, 10363. (u) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1997, 44, 125.
68. Some representative articles on this subject: (a) Welch, S. C.; Wong, R. Y. Tetrahedron Lett. 1972, 1855. (b) Yamakawa, K.; Kurita, J.; Sakaguchi, R. Tetrahedron Lett. 1973, 3877. Goldsmith, D. J.; Lewis, A. J.; Still, W. C., Jr. Tetrahedron Lett. 1973, 4807. Masuoka, N.; Kamikawa, T.; Kubota, T. Chem. Lett. 1974, 751. (e) Fujimoto, Y.; Yokura, S.; Nakamura, T.; Morikawa, T.; Tatsuno, T. Tetrahedron Lett. 1974, 2523. (f) Masuoka, N.; Kamikawa, T. Tetrahedron Lett. 1976, 1691. (g) Yamakawa, K.; Sakaguchi, R.; Nakamura, T.; Watanabe, K. Chem. Lett. 1976, 991. (h) Colvin, E. W.; Malchenko, S.; Raphael, R. A.; Roberts, J. S. J. Chem. Soc., Perkin Trans. 1, 1978, 658. Nakahara, Y.; Tatsuno, T. Chem. Pharm. Bull. 1980, 28, 1981. (j) Goldsmith, D. J.; John, T. K.; Kwong, C. D.; Painter, G. R. J. Org. Chem. 1980, 45, 3989. (k) Kraus, G. A.; Frazier, K. J. Org. Chem. 1980, 45, 4820. Kraus, G. A.; Roth, B. J. Org. Chem. 1980, 45, 4825. (n) White, J. D.; Matsui, T.; Thomas, J. A. J. Org. Chem. 1981, 46, 3376. (o) Pearson, A. J.; Ong, C. W. J. Am. Chem. Soc. 1981, 103, 6686. (p) Ziegler, F. E.; Nangia, A.; Schulte, G. J. Am. Chem. Soc. 1987, 109, 3987. (q) Colvin, E. W.; Egan, M. J.; Kerr, F. W. J. Chem. Soc., Chem. Commun. 1990, 1200. (r) Ziegler, F. E.; Sobolov, S. B. J. Am. Chem. Soc. 1990, 112, 2749. (s) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1996, 42, 165. (t) Nemoto, H.; Miyata, J. Fukumoto, K. Tetrahedron, 1996, 52, 10363. (u) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1997, 44, 125.
69. Some representative articles on this subject: (a) Welch, S. C.; Wong, R. Y. Tetrahedron Lett. 1972, 1855. (b) Yamakawa, K.; Kurita, J.; Sakaguchi, R. Tetrahedron Lett. 1973, 3877. Goldsmith, D. J.; Lewis, A. J.; Still, W. C., Jr. Tetrahedron Lett. 1973, 4807. Masuoka, N.; Kamikawa, T.; Kubota, T. Chem. Lett. 1974, 751. (e) Fujimoto, Y.; Yokura, S.; Nakamura, T.; Morikawa, T.; Tatsuno, T. Tetrahedron Lett. 1974, 2523. (f) Masuoka, N.; Kamikawa, T. Tetrahedron Lett. 1976, 1691. (g) Yamakawa, K.; Sakaguchi, R.; Nakamura, T.; Watanabe, K. Chem. Lett. 1976, 991. (h) Colvin, E. W.; Malchenko, S.; Raphael, R. A.; Roberts, J. S. J. Chem. Soc., Perkin Trans. 1, 1978, 658. Nakahara, Y.; Tatsuno, T. Chem. Pharm. Bull. 1980, 28, 1981. (j) Goldsmith, D. J.; John, T. K.; Kwong, C. D.; Painter, G. R. J. Org. Chem. 1980, 45, 3989. (k) Kraus, G. A.; Frazier, K. J. Org. Chem. 1980, 45, 4820. Kraus, G. A.; Roth, B. J. Org. Chem. 1980, 45, 4825. (n) White, J. D.; Matsui, T.; Thomas, J. A. J. Org. Chem. 1981, 46, 3376. (o) Pearson, A. J.; Ong, C. W. J. Am. Chem. Soc. 1981, 103, 6686. (p) Ziegler, F. E.; Nangia, A.; Schulte, G. J. Am. Chem. Soc. 1987, 109, 3987. (q) Colvin, E. W.; Egan, M. J.; Kerr, F. W. J. Chem. Soc., Chem. Commun. 1990, 1200. (r) Ziegler, F. E.; Sobolov, S. B. J. Am. Chem. Soc. 1990, 112, 2749. (s) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1996, 42, 165. (t) Nemoto, H.; Miyata, J. Fukumoto, K. Tetrahedron, 1996, 52, 10363. (u) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1997, 44, 125.
70. Some representative articles on this subject: (a) Welch, S. C.; Wong, R. Y. Tetrahedron Lett. 1972, 1855. (b) Yamakawa, K.; Kurita, J.; Sakaguchi, R. Tetrahedron Lett. 1973, 3877. Goldsmith, D. J.; Lewis, A. J.; Still, W. C., Jr. Tetrahedron Lett. 1973, 4807. Masuoka, N.; Kamikawa, T.; Kubota, T. Chem. Lett. 1974, 751. (e) Fujimoto, Y.; Yokura, S.; Nakamura, T.; Morikawa, T.; Tatsuno, T. Tetrahedron Lett. 1974, 2523. (f) Masuoka, N.; Kamikawa, T. Tetrahedron Lett. 1976, 1691. (g) Yamakawa, K.; Sakaguchi, R.; Nakamura, T.; Watanabe, K. Chem. Lett. 1976, 991. (h) Colvin, E. W.; Malchenko, S.; Raphael, R. A.; Roberts, J. S. J. Chem. Soc., Perkin Trans. 1, 1978, 658. Nakahara, Y.; Tatsuno, T. Chem. Pharm. Bull. 1980, 28, 1981. (j) Goldsmith, D. J.; John, T. K.; Kwong, C. D.; Painter, G. R. J. Org. Chem. 1980, 45, 3989. (k) Kraus, G. A.; Frazier, K. J. Org. Chem. 1980, 45, 4820. Kraus, G. A.; Roth, B. J. Org. Chem. 1980, 45, 4825. (n) White, J. D.; Matsui, T.; Thomas, J. A. J. Org. Chem. 1981, 46, 3376. (o) Pearson, A. J.; Ong, C. W. J. Am. Chem. Soc. 1981, 103, 6686. (p) Ziegler, F. E.; Nangia, A.; Schulte, G. J. Am. Chem. Soc. 1987, 109, 3987. (q) Colvin, E. W.; Egan, M. J.; Kerr, F. W. J. Chem. Soc., Chem. Commun. 1990, 1200. (r) Ziegler, F. E.; Sobolov, S. B. J. Am. Chem. Soc. 1990, 112, 2749. (s) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1996, 42, 165. (t) Nemoto, H.; Miyata, J. Fukumoto, K. Tetrahedron, 1996, 52, 10363. (u) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1997, 44, 125.
71. Some representative articles on this subject: (a) Welch, S. C.; Wong, R. Y. Tetrahedron Lett. 1972, 1855. (b) Yamakawa, K.; Kurita, J.; Sakaguchi, R. Tetrahedron Lett. 1973, 3877. Goldsmith, D. J.; Lewis, A. J.; Still, W. C., Jr. Tetrahedron Lett. 1973, 4807. Masuoka, N.; Kamikawa, T.; Kubota, T. Chem. Lett. 1974, 751. (e) Fujimoto, Y.; Yokura, S.; Nakamura, T.; Morikawa, T.; Tatsuno, T. Tetrahedron Lett. 1974, 2523. (f) Masuoka, N.; Kamikawa, T. Tetrahedron Lett. 1976, 1691. (g) Yamakawa, K.; Sakaguchi, R.; Nakamura, T.; Watanabe, K. Chem. Lett. 1976, 991. (h) Colvin, E. W.; Malchenko, S.; Raphael, R. A.; Roberts, J. S. J. Chem. Soc., Perkin Trans. 1, 1978, 658. Nakahara, Y.; Tatsuno, T. Chem. Pharm. Bull. 1980, 28, 1981. (j) Goldsmith, D. J.; John, T. K.; Kwong, C. D.; Painter, G. R. J. Org. Chem. 1980, 45, 3989. (k) Kraus, G. A.; Frazier, K. J. Org. Chem. 1980, 45, 4820. Kraus, G. A.; Roth, B. J. Org. Chem. 1980, 45, 4825. (n) White, J. D.; Matsui, T.; Thomas, J. A. J. Org. Chem. 1981, 46, 3376. (o) Pearson, A. J.; Ong, C. W. J. Am. Chem. Soc. 1981, 103, 6686. (p) Ziegler, F. E.; Nangia, A.; Schulte, G. J. Am. Chem. Soc. 1987, 109, 3987. (q) Colvin, E. W.; Egan, M. J.; Kerr, F. W. J. Chem. Soc., Chem. Commun. 1990, 1200. (r) Ziegler, F. E.; Sobolov, S. B. J. Am. Chem. Soc. 1990, 112, 2749. (s) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1996, 42, 165. (t) Nemoto, H.; Miyata, J. Fukumoto, K. Tetrahedron, 1996, 52, 10363. (u) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1997, 44, 125.
72. Some representative articles on this subject: (a) Welch, S. C.; Wong, R. Y. Tetrahedron Lett. 1972, 1855. (b) Yamakawa, K.; Kurita, J.; Sakaguchi, R. Tetrahedron Lett. 1973, 3877. Goldsmith, D. J.; Lewis, A. J.; Still, W. C., Jr. Tetrahedron Lett. 1973, 4807. Masuoka, N.; Kamikawa, T.; Kubota, T. Chem. Lett. 1974, 751. (e) Fujimoto, Y.; Yokura, S.; Nakamura, T.; Morikawa, T.; Tatsuno, T. Tetrahedron Lett. 1974, 2523. (f) Masuoka, N.; Kamikawa, T. Tetrahedron Lett. 1976, 1691. (g) Yamakawa, K.; Sakaguchi, R.; Nakamura, T.; Watanabe, K. Chem. Lett. 1976, 991. (h) Colvin, E. W.; Malchenko, S.; Raphael, R. A.; Roberts, J. S. J. Chem. Soc., Perkin Trans. 1, 1978, 658. Nakahara, Y.; Tatsuno, T. Chem. Pharm. Bull. 1980, 28, 1981. (j) Goldsmith, D. J.; John, T. K.; Kwong, C. D.; Painter, G. R. J. Org. Chem. 1980, 45, 3989. (k) Kraus, G. A.; Frazier, K. J. Org. Chem. 1980, 45, 4820. Kraus, G. A.; Roth, B. J. Org. Chem. 1980, 45, 4825. (n) White, J. D.; Matsui, T.; Thomas, J. A. J. Org. Chem. 1981, 46, 3376. (o) Pearson, A. J.; Ong, C. W. J. Am. Chem. Soc. 1981, 103, 6686. (p) Ziegler, F. E.; Nangia, A.; Schulte, G. J. Am. Chem. Soc. 1987, 109, 3987. (q) Colvin, E. W.; Egan, M. J.; Kerr, F. W. J. Chem. Soc., Chem. Commun. 1990, 1200. (r) Ziegler, F. E.; Sobolov, S. B. J. Am. Chem. Soc. 1990, 112, 2749. (s) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1996, 42, 165. (t) Nemoto, H.; Miyata, J. Fukumoto, K. Tetrahedron, 1996, 52, 10363. (u) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1997, 44, 125.
73. Some representative articles on this subject: (a) Welch, S. C.; Wong, R. Y. Tetrahedron Lett. 1972, 1855. (b) Yamakawa, K.; Kurita, J.; Sakaguchi, R. Tetrahedron Lett. 1973, 3877. Goldsmith, D. J.; Lewis, A. J.; Still, W. C., Jr. Tetrahedron Lett. 1973, 4807. Masuoka, N.; Kamikawa, T.; Kubota, T. Chem. Lett. 1974, 751. (e) Fujimoto, Y.; Yokura, S.; Nakamura, T.; Morikawa, T.; Tatsuno, T. Tetrahedron Lett. 1974, 2523. (f) Masuoka, N.; Kamikawa, T. Tetrahedron Lett. 1976, 1691. (g) Yamakawa, K.; Sakaguchi, R.; Nakamura, T.; Watanabe, K. Chem. Lett. 1976, 991. (h) Colvin, E. W.; Malchenko, S.; Raphael, R. A.; Roberts, J. S. J. Chem. Soc., Perkin Trans. 1, 1978, 658. Nakahara, Y.; Tatsuno, T. Chem. Pharm. Bull. 1980, 28, 1981. (j) Goldsmith, D. J.; John, T. K.; Kwong, C. D.; Painter, G. R. J. Org. Chem. 1980, 45, 3989. (k) Kraus, G. A.; Frazier, K. J. Org. Chem. 1980, 45, 4820. Kraus, G. A.; Roth, B. J. Org. Chem. 1980, 45, 4825. (n) White, J. D.; Matsui, T.; Thomas, J. A. J. Org. Chem. 1981, 46, 3376. (o) Pearson, A. J.; Ong, C. W. J. Am. Chem. Soc. 1981, 103, 6686. (p) Ziegler, F. E.; Nangia, A.; Schulte, G. J. Am. Chem. Soc. 1987, 109, 3987. (q) Colvin, E. W.; Egan, M. J.; Kerr, F. W. J. Chem. Soc., Chem. Commun. 1990, 1200. (r) Ziegler, F. E.; Sobolov, S. B. J. Am. Chem. Soc. 1990, 112, 2749. (s) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1996, 42, 165. (t) Nemoto, H.; Miyata, J. Fukumoto, K. Tetrahedron, 1996, 52, 10363. (u) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1997, 44, 125.
74. Some representative articles on this subject: (a) Welch, S. C.; Wong, R. Y. Tetrahedron Lett. 1972, 1855. (b) Yamakawa, K.; Kurita, J.; Sakaguchi, R. Tetrahedron Lett. 1973, 3877. Goldsmith, D. J.; Lewis, A. J.; Still, W. C., Jr. Tetrahedron Lett. 1973, 4807. Masuoka, N.; Kamikawa, T.; Kubota, T. Chem. Lett. 1974, 751. (e) Fujimoto, Y.; Yokura, S.; Nakamura, T.; Morikawa, T.; Tatsuno, T. Tetrahedron Lett. 1974, 2523. (f) Masuoka, N.; Kamikawa, T. Tetrahedron Lett. 1976, 1691. (g) Yamakawa, K.; Sakaguchi, R.; Nakamura, T.; Watanabe, K. Chem. Lett. 1976, 991. (h) Colvin, E. W.; Malchenko, S.; Raphael, R. A.; Roberts, J. S. J. Chem. Soc., Perkin Trans. 1, 1978, 658. Nakahara, Y.; Tatsuno, T. Chem. Pharm. Bull. 1980, 28, 1981. (j) Goldsmith, D. J.; John, T. K.; Kwong, C. D.; Painter, G. R. J. Org. Chem. 1980, 45, 3989. (k) Kraus, G. A.; Frazier, K. J. Org. Chem. 1980, 45, 4820. Kraus, G. A.; Roth, B. J. Org. Chem. 1980, 45, 4825. (n) White, J. D.; Matsui, T.; Thomas, J. A. J. Org. Chem. 1981, 46, 3376. (o) Pearson, A. J.; Ong, C. W. J. Am. Chem. Soc. 1981, 103, 6686. (p) Ziegler, F. E.; Nangia, A.; Schulte, G. J. Am. Chem. Soc. 1987, 109, 3987. (q) Colvin, E. W.; Egan, M. J.; Kerr, F. W. J. Chem. Soc., Chem. Commun. 1990, 1200. (r) Ziegler, F. E.; Sobolov, S. B. J. Am. Chem. Soc. 1990, 112, 2749. (s) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1996, 42, 165. (t) Nemoto, H.; Miyata, J. Fukumoto, K. Tetrahedron, 1996, 52, 10363. (u) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1997, 44, 125.
75. Some representative articles on this subject: (a) Welch, S. C.; Wong, R. Y. Tetrahedron Lett. 1972, 1855. (b) Yamakawa, K.; Kurita, J.; Sakaguchi, R. Tetrahedron Lett. 1973, 3877. Goldsmith, D. J.; Lewis, A. J.; Still, W. C., Jr. Tetrahedron Lett. 1973, 4807. Masuoka, N.; Kamikawa, T.; Kubota, T. Chem. Lett. 1974, 751. (e) Fujimoto, Y.; Yokura, S.; Nakamura, T.; Morikawa, T.; Tatsuno, T. Tetrahedron Lett. 1974, 2523. (f) Masuoka, N.; Kamikawa, T. Tetrahedron Lett. 1976, 1691. (g) Yamakawa, K.; Sakaguchi, R.; Nakamura, T.; Watanabe, K. Chem. Lett. 1976, 991. (h) Colvin, E. W.; Malchenko, S.; Raphael, R. A.; Roberts, J. S. J. Chem. Soc., Perkin Trans. 1, 1978, 658. Nakahara, Y.; Tatsuno, T. Chem. Pharm. Bull. 1980, 28, 1981. (j) Goldsmith, D. J.; John, T. K.; Kwong, C. D.; Painter, G. R. J. Org. Chem. 1980, 45, 3989. (k) Kraus, G. A.; Frazier, K. J. Org. Chem. 1980, 45, 4820. Kraus, G. A.; Roth, B. J. Org. Chem. 1980, 45, 4825. (n) White, J. D.; Matsui, T.; Thomas, J. A. J. Org. Chem. 1981, 46, 3376. (o) Pearson, A. J.; Ong, C. W. J. Am. Chem. Soc. 1981, 103, 6686. (p) Ziegler, F. E.; Nangia, A.; Schulte, G. J. Am. Chem. Soc. 1987, 109, 3987. (q) Colvin, E. W.; Egan, M. J.; Kerr, F. W. J. Chem. Soc., Chem. Commun. 1990, 1200. (r) Ziegler, F. E.; Sobolov, S. B. J. Am. Chem. Soc. 1990, 112, 2749. (s) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1996, 42, 165. (t) Nemoto, H.; Miyata, J. Fukumoto, K. Tetrahedron, 1996, 52, 10363. (u) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1997, 44, 125.
76. Some representative articles on this subject: (a) Welch, S. C.; Wong, R. Y. Tetrahedron Lett. 1972, 1855. (b) Yamakawa, K.; Kurita, J.; Sakaguchi, R. Tetrahedron Lett. 1973, 3877. Goldsmith, D. J.; Lewis, A. J.; Still, W. C., Jr. Tetrahedron Lett. 1973, 4807. Masuoka, N.; Kamikawa, T.; Kubota, T. Chem. Lett. 1974, 751. (e) Fujimoto, Y.; Yokura, S.; Nakamura, T.; Morikawa, T.; Tatsuno, T. Tetrahedron Lett. 1974, 2523. (f) Masuoka, N.; Kamikawa, T. Tetrahedron Lett. 1976, 1691. (g) Yamakawa, K.; Sakaguchi, R.; Nakamura, T.; Watanabe, K. Chem. Lett. 1976, 991. (h) Colvin, E. W.; Malchenko, S.; Raphael, R. A.; Roberts, J. S. J. Chem. Soc., Perkin Trans. 1, 1978, 658. Nakahara, Y.; Tatsuno, T. Chem. Pharm. Bull. 1980, 28, 1981. (j) Goldsmith, D. J.; John, T. K.; Kwong, C. D.; Painter, G. R. J. Org. Chem. 1980, 45, 3989. (k) Kraus, G. A.; Frazier, K. J. Org. Chem. 1980, 45, 4820. Kraus, G. A.; Roth, B. J. Org. Chem. 1980, 45, 4825. (n) White, J. D.; Matsui, T.; Thomas, J. A. J. Org. Chem. 1981, 46, 3376. (o) Pearson, A. J.; Ong, C. W. J. Am. Chem. Soc. 1981, 103, 6686. (p) Ziegler, F. E.; Nangia, A.; Schulte, G. J. Am. Chem. Soc. 1987, 109, 3987. (q) Colvin, E. W.; Egan, M. J.; Kerr, F. W. J. Chem. Soc., Chem. Commun. 1990, 1200. (r) Ziegler, F. E.; Sobolov, S. B. J. Am. Chem. Soc. 1990, 112, 2749. (s) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1996, 42, 165. (t) Nemoto, H.; Miyata, J. Fukumoto, K. Tetrahedron, 1996, 52, 10363. (u) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1997, 44, 125.
77. Some representative articles on this subject: (a) Welch, S. C.; Wong, R. Y. Tetrahedron Lett. 1972, 1855. (b) Yamakawa, K.; Kurita, J.; Sakaguchi, R. Tetrahedron Lett. 1973, 3877. Goldsmith, D. J.; Lewis, A. J.; Still, W. C., Jr. Tetrahedron Lett. 1973, 4807. Masuoka, N.; Kamikawa, T.; Kubota, T. Chem. Lett. 1974, 751. (e) Fujimoto, Y.; Yokura, S.; Nakamura, T.; Morikawa, T.; Tatsuno, T. Tetrahedron Lett. 1974, 2523. (f) Masuoka, N.; Kamikawa, T. Tetrahedron Lett. 1976, 1691. (g) Yamakawa, K.; Sakaguchi, R.; Nakamura, T.; Watanabe, K. Chem. Lett. 1976, 991. (h) Colvin, E. W.; Malchenko, S.; Raphael, R. A.; Roberts, J. S. J. Chem. Soc., Perkin Trans. 1, 1978, 658. Nakahara, Y.; Tatsuno, T. Chem. Pharm. Bull. 1980, 28, 1981. (j) Goldsmith, D. J.; John, T. K.; Kwong, C. D.; Painter, G. R. J. Org. Chem. 1980, 45, 3989. (k) Kraus, G. A.; Frazier, K. J. Org. Chem. 1980, 45, 4820. Kraus, G. A.; Roth, B. J. Org. Chem. 1980, 45, 4825. (n) White, J. D.; Matsui, T.; Thomas, J. A. J. Org. Chem. 1981, 46, 3376. (o) Pearson, A. J.; Ong, C. W. J. Am. Chem. Soc. 1981, 103, 6686. (p) Ziegler, F. E.; Nangia, A.; Schulte, G. J. Am. Chem. Soc. 1987, 109, 3987. (q) Colvin, E. W.; Egan, M. J.; Kerr, F. W. J. Chem. Soc., Chem. Commun. 1990, 1200. (r) Ziegler, F. E.; Sobolov, S. B. J. Am. Chem. Soc. 1990, 112, 2749. (s) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1996, 42, 165. (t) Nemoto, H.; Miyata, J. Fukumoto, K. Tetrahedron, 1996, 52, 10363. (u) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1997, 44, 125.
78. Some representative articles on this subject: (a) Welch, S. C.; Wong, R. Y. Tetrahedron Lett. 1972, 1855. (b) Yamakawa, K.; Kurita, J.; Sakaguchi, R. Tetrahedron Lett. 1973, 3877. Goldsmith, D. J.; Lewis, A. J.; Still, W. C., Jr. Tetrahedron Lett. 1973, 4807. Masuoka, N.; Kamikawa, T.; Kubota, T. Chem. Lett. 1974, 751. (e) Fujimoto, Y.; Yokura, S.; Nakamura, T.; Morikawa, T.; Tatsuno, T. Tetrahedron Lett. 1974, 2523. (f) Masuoka, N.; Kamikawa, T. Tetrahedron Lett. 1976, 1691. (g) Yamakawa, K.; Sakaguchi, R.; Nakamura, T.; Watanabe, K. Chem. Lett. 1976, 991. (h) Colvin, E. W.; Malchenko, S.; Raphael, R. A.; Roberts, J. S. J. Chem. Soc., Perkin Trans. 1, 1978, 658. Nakahara, Y.; Tatsuno, T. Chem. Pharm. Bull. 1980, 28, 1981. (j) Goldsmith, D. J.; John, T. K.; Kwong, C. D.; Painter, G. R. J. Org. Chem. 1980, 45, 3989. (k) Kraus, G. A.; Frazier, K. J. Org. Chem. 1980, 45, 4820. Kraus, G. A.; Roth, B. J. Org. Chem. 1980, 45, 4825. (n) White, J. D.; Matsui, T.; Thomas, J. A. J. Org. Chem. 1981, 46, 3376. (o) Pearson, A. J.; Ong, C. W. J. Am. Chem. Soc. 1981, 103, 6686. (p) Ziegler, F. E.; Nangia, A.; Schulte, G. J. Am. Chem. Soc. 1987, 109, 3987. (q) Colvin, E. W.; Egan, M. J.; Kerr, F. W. J. Chem. Soc., Chem. Commun. 1990, 1200. (r) Ziegler, F. E.; Sobolov, S. B. J. Am. Chem. Soc. 1990, 112, 2749. (s) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1996, 42, 165. (t) Nemoto, H.; Miyata, J. Fukumoto, K. Tetrahedron, 1996, 52, 10363. (u) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1997, 44, 125.
79. Some representative articles on this subject: (a) Welch, S. C.; Wong, R. Y. Tetrahedron Lett. 1972, 1855. (b) Yamakawa, K.; Kurita, J.; Sakaguchi, R. Tetrahedron Lett. 1973, 3877. Goldsmith, D. J.; Lewis, A. J.; Still, W. C., Jr. Tetrahedron Lett. 1973, 4807. Masuoka, N.; Kamikawa, T.; Kubota, T. Chem. Lett. 1974, 751. (e) Fujimoto, Y.; Yokura, S.; Nakamura, T.; Morikawa, T.; Tatsuno, T. Tetrahedron Lett. 1974, 2523. (f) Masuoka, N.; Kamikawa, T. Tetrahedron Lett. 1976, 1691. (g) Yamakawa, K.; Sakaguchi, R.; Nakamura, T.; Watanabe, K. Chem. Lett. 1976, 991. (h) Colvin, E. W.; Malchenko, S.; Raphael, R. A.; Roberts, J. S. J. Chem. Soc., Perkin Trans. 1, 1978, 658. Nakahara, Y.; Tatsuno, T. Chem. Pharm. Bull. 1980, 28, 1981. (j) Goldsmith, D. J.; John, T. K.; Kwong, C. D.; Painter, G. R. J. Org. Chem. 1980, 45, 3989. (k) Kraus, G. A.; Frazier, K. J. Org. Chem. 1980, 45, 4820. Kraus, G. A.; Roth, B. J. Org. Chem. 1980, 45, 4825. (n) White, J. D.; Matsui, T.; Thomas, J. A. J. Org. Chem. 1981, 46, 3376. (o) Pearson, A. J.; Ong, C. W. J. Am. Chem. Soc. 1981, 103, 6686. (p) Ziegler, F. E.; Nangia, A.; Schulte, G. J. Am. Chem. Soc. 1987, 109, 3987. (q) Colvin, E. W.; Egan, M. J.; Kerr, F. W. J. Chem. Soc., Chem. Commun. 1990, 1200. (r) Ziegler, F. E.; Sobolov, S. B. J. Am. Chem. Soc. 1990, 112, 2749. (s) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1996, 42, 165. (t) Nemoto, H.; Miyata, J. Fukumoto, K. Tetrahedron, 1996, 52, 10363. (u) Nemoto, H.; Miyata, J. Fukumoto, K. Hetereocycles, 1997, 44, 125.
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99. Some recent applications of the Barton's radically induced decarboxylation for natural products synthesis: Corey, E. J.; Hong, B.-c. J. Am. Chem. Soc. 1994, 116, 3149; Hatakeyama, S.; Kawamura, M.; Takano, S. J. Am. Chem. Soc. 1994, 116, 4081; Schultz, A. G.; Holoboski, M. A.; Smyth, M. S. J. Am. Chem. Soc. 1996, 118, 6120; Trost, B. M.; Higuchi, R. I. J. Am. Chem. Soc. 1996, 118, 10094. Stamos, D. P.; Chen, S. S.; Kishi, Y. J. Org. Chem. 1997, 62, 7552.
100. Some recent applications of the Barton's radically induced decarboxylation for natural products synthesis: Corey, E. J.; Hong, B.-c. J. Am. Chem. Soc. 1994, 116, 3149; Hatakeyama, S.; Kawamura, M.; Takano, S. J. Am. Chem. Soc. 1994, 116, 4081; Schultz, A. G.; Holoboski, M. A.; Smyth, M. S. J. Am. Chem. Soc. 1996, 118, 6120; Trost, B. M.; Higuchi, R. I. J. Am. Chem. Soc. 1996, 118, 10094. Stamos, D. P.; Chen, S. S.; Kishi, Y. J. Org. Chem. 1997, 62, 7552.
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102. Some recent applications of the Barton's radically induced decarboxylation for natural products synthesis: Corey, E. J.; Hong, B.-c. J. Am. Chem. Soc. 1994, 116, 3149; Hatakeyama, S.; Kawamura, M.; Takano, S. J. Am. Chem. Soc. 1994, 116, 4081; Schultz, A. G.; Holoboski, M. A.; Smyth, M. S. J. Am. Chem. Soc. 1996, 118, 6120; Trost, B. M.; Higuchi, R. I. J. Am. Chem. Soc. 1996, 118, 10094. Stamos, D. P.; Chen, S. S.; Kishi, Y. J. Org. Chem. 1997, 62, 7552.
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