Novel access to neopentyl-type halogenated cyclopentanoids via olefinic cyclobutanols

Journal of Organic Chemistry

Volumn 61, Issue 4, 1996, Pages 1347-1348

  Nemoto, Hideo ^a   Shiraki, Motohiro ^a   Fukumoto, Keiichiro ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOBUTANE DERIVATIVE; CYCLOPENTANONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029863801     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951806y     Document Type: Article

References (53)

1. For naturally occurring cyclopentanoids: (a) Devon, T. K.; Scott, A. I. Handbook of Naturally Occurring Compounds; Academic Press: New York, 1972, Vols. I and II. (b) Nakanishi, K.; Goto, T.; Ito, S.; Nozoe, S. Natural Products Chemistry; Kodansha Scientific, Tokyo, 1974, Vol. I. (c) Corner, F. W.; McCapra, F.; Qureshi, I. H.; Scott, A. I. Tetrahedron 1967, 23, 4761. (d) Seto, H.; Yonehara, H. J. Antibiot. 1980, 33, 92. (e) Cane, D. E.; Oliver, J. S.; Harrison, P. H. M.; Abell, C.; Hubbard, B. R; Kane, C. T.; Lattman, R. J. Am. Chem. Soc. 1990, 112, 4513. For Carbocyclic nucleosides: (f) Marquez, V. E.; Lim, M.-I. Med Res. Rev. 1986, 611. (g) Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48, 571. (h) Niitsuma, S.; Ichikawa, Y.-I.; Takita, T. Studies in Natural Products Chemistry; Elsevier Science BV Amsterdam, 1992; p 585.
2. For naturally occurring cyclopentanoids: (a) Devon, T. K.; Scott, A. I. Handbook of Naturally Occurring Compounds; Academic Press: New York, 1972, Vols. I and II. (b) Nakanishi, K.; Goto, T.; Ito, S.; Nozoe, S. Natural Products Chemistry; Kodansha Scientific, Tokyo, 1974, Vol. I. (c) Corner, F. W.; McCapra, F.; Qureshi, I. H.; Scott, A. I. Tetrahedron 1967, 23, 4761. (d) Seto, H.; Yonehara, H. J. Antibiot. 1980, 33, 92. (e) Cane, D. E.; Oliver, J. S.; Harrison, P. H. M.; Abell, C.; Hubbard, B. R; Kane, C. T.; Lattman, R. J. Am. Chem. Soc. 1990, 112, 4513. For Carbocyclic nucleosides: (f) Marquez, V. E.; Lim, M.-I. Med Res. Rev. 1986, 611. (g) Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48, 571. (h) Niitsuma, S.; Ichikawa, Y.-I.; Takita, T. Studies in Natural Products Chemistry; Elsevier Science BV Amsterdam, 1992; p 585.
3. For naturally occurring cyclopentanoids: (a) Devon, T. K.; Scott, A. I. Handbook of Naturally Occurring Compounds; Academic Press: New York, 1972, Vols. I and II. (b) Nakanishi, K.; Goto, T.; Ito, S.; Nozoe, S. Natural Products Chemistry; Kodansha Scientific, Tokyo, 1974, Vol. I. (c) Corner, F. W.; McCapra, F.; Qureshi, I. H.; Scott, A. I. Tetrahedron 1967, 23, 4761. (d) Seto, H.; Yonehara, H. J. Antibiot. 1980, 33, 92. (e) Cane, D. E.; Oliver, J. S.; Harrison, P. H. M.; Abell, C.; Hubbard, B. R; Kane, C. T.; Lattman, R. J. Am. Chem. Soc. 1990, 112, 4513. For Carbocyclic nucleosides: (f) Marquez, V. E.; Lim, M.-I. Med Res. Rev. 1986, 611. (g) Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48, 571. (h) Niitsuma, S.; Ichikawa, Y.-I.; Takita, T. Studies in Natural Products Chemistry; Elsevier Science BV Amsterdam, 1992; p 585.
4. For naturally occurring cyclopentanoids: (a) Devon, T. K.; Scott, A. I. Handbook of Naturally Occurring Compounds; Academic Press: New York, 1972, Vols. I and II. (b) Nakanishi, K.; Goto, T.; Ito, S.; Nozoe, S. Natural Products Chemistry; Kodansha Scientific, Tokyo, 1974, Vol. I. (c) Corner, F. W.; McCapra, F.; Qureshi, I. H.; Scott, A. I. Tetrahedron 1967, 23, 4761. (d) Seto, H.; Yonehara, H. J. Antibiot. 1980, 33, 92. (e) Cane, D. E.; Oliver, J. S.; Harrison, P. H. M.; Abell, C.; Hubbard, B. R; Kane, C. T.; Lattman, R. J. Am. Chem. Soc. 1990, 112, 4513. For Carbocyclic nucleosides: (f) Marquez, V. E.; Lim, M.-I. Med Res. Rev. 1986, 611. (g) Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48, 571. (h) Niitsuma, S.; Ichikawa, Y.-I.; Takita, T. Studies in Natural Products Chemistry; Elsevier Science BV Amsterdam, 1992; p 585.
5. For naturally occurring cyclopentanoids: (a) Devon, T. K.; Scott, A. I. Handbook of Naturally Occurring Compounds; Academic Press: New York, 1972, Vols. I and II. (b) Nakanishi, K.; Goto, T.; Ito, S.; Nozoe, S. Natural Products Chemistry; Kodansha Scientific, Tokyo, 1974, Vol. I. (c) Corner, F. W.; McCapra, F.; Qureshi, I. H.; Scott, A. I. Tetrahedron 1967, 23, 4761. (d) Seto, H.; Yonehara, H. J. Antibiot. 1980, 33, 92. (e) Cane, D. E.; Oliver, J. S.; Harrison, P. H. M.; Abell, C.; Hubbard, B. R; Kane, C. T.; Lattman, R. J. Am. Chem. Soc. 1990, 112, 4513. For Carbocyclic nucleosides: (f) Marquez, V. E.; Lim, M.-I. Med Res. Rev. 1986, 611. (g) Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48, 571. (h) Niitsuma, S.; Ichikawa, Y.-I.; Takita, T. Studies in Natural Products Chemistry; Elsevier Science BV Amsterdam, 1992; p 585.
6. For naturally occurring cyclopentanoids: (a) Devon, T. K.; Scott, A. I. Handbook of Naturally Occurring Compounds; Academic Press: New York, 1972, Vols. I and II. (b) Nakanishi, K.; Goto, T.; Ito, S.; Nozoe, S. Natural Products Chemistry; Kodansha Scientific, Tokyo, 1974, Vol. I. (c) Corner, F. W.; McCapra, F.; Qureshi, I. H.; Scott, A. I. Tetrahedron 1967, 23, 4761. (d) Seto, H.; Yonehara, H. J. Antibiot. 1980, 33, 92. (e) Cane, D. E.; Oliver, J. S.; Harrison, P. H. M.; Abell, C.; Hubbard, B. R; Kane, C. T.; Lattman, R. J. Am. Chem. Soc. 1990, 112, 4513. For Carbocyclic nucleosides: (f) Marquez, V. E.; Lim, M.-I. Med Res. Rev. 1986, 611. (g) Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48, 571. (h) Niitsuma, S.; Ichikawa, Y.-I.; Takita, T. Studies in Natural Products Chemistry; Elsevier Science BV Amsterdam, 1992; p 585.
7. For naturally occurring cyclopentanoids: (a) Devon, T. K.; Scott, A. I. Handbook of Naturally Occurring Compounds; Academic Press: New York, 1972, Vols. I and II. (b) Nakanishi, K.; Goto, T.; Ito, S.; Nozoe, S. Natural Products Chemistry; Kodansha Scientific, Tokyo, 1974, Vol. I. (c) Corner, F. W.; McCapra, F.; Qureshi, I. H.; Scott, A. I. Tetrahedron 1967, 23, 4761. (d) Seto, H.; Yonehara, H. J. Antibiot. 1980, 33, 92. (e) Cane, D. E.; Oliver, J. S.; Harrison, P. H. M.; Abell, C.; Hubbard, B. R; Kane, C. T.; Lattman, R. J. Am. Chem. Soc. 1990, 112, 4513. For Carbocyclic nucleosides: (f) Marquez, V. E.; Lim, M.-I. Med Res. Rev. 1986, 611. (g) Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48, 571. (h) Niitsuma, S.; Ichikawa, Y.-I.; Takita, T. Studies in Natural Products Chemistry; Elsevier Science BV Amsterdam, 1992; p 585.
8. For naturally occurring cyclopentanoids: (a) Devon, T. K.; Scott, A. I. Handbook of Naturally Occurring Compounds; Academic Press: New York, 1972, Vols. I and II. (b) Nakanishi, K.; Goto, T.; Ito, S.; Nozoe, S. Natural Products Chemistry; Kodansha Scientific, Tokyo, 1974, Vol. I. (c) Corner, F. W.; McCapra, F.; Qureshi, I. H.; Scott, A. I. Tetrahedron 1967, 23, 4761. (d) Seto, H.; Yonehara, H. J. Antibiot. 1980, 33, 92. (e) Cane, D. E.; Oliver, J. S.; Harrison, P. H. M.; Abell, C.; Hubbard, B. R; Kane, C. T.; Lattman, R. J. Am. Chem. Soc. 1990, 112, 4513. For Carbocyclic nucleosides: (f) Marquez, V. E.; Lim, M.-I. Med Res. Rev. 1986, 611. (g) Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48, 571. (h) Niitsuma, S.; Ichikawa, Y.-I.; Takita, T. Studies in Natural Products Chemistry; Elsevier Science BV Amsterdam, 1992; p 585.
9. For reviews in this area, see: (a) The Total Synthesis of Natural Products ApSimon, J. W. Ed., John Wiley & Sons: New York: 1973; Vol. 1, p 81; 1973, Vol. 2, p 1, p 197, 1981, Vol. 4, p 353, p 451; 1983, Vol. 5, p 1; 1983, Vol. 7, p 275. (b) Mitra, A. The Synthesis of Prostaglandins; John Wiley & Sons: New York, 1977. (c) Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. (d) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer Verlag: Berlin, 1987. (e) Ramaiah, M. Synthesis 1984, 529. (f) Paquette, L. A. Top. Curr. Chem. 1984, 119, 1. (g) Curran, D. P. Synthesis 1988, 417, 489. (h) Shore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 1037. For some recent studies on this area, see: (i) Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. (j) Negishi, E.; Jensen, M. D.; Kondakov, D. Y.; Wang, S. J. Am. Chem. Soc. 1994, 116, 8404. (k) Lee, B. Y.; Chung, Y. K. J. Am Chem. Soc. 1994, 116, 8793. (l) Sturino, C. F.; Fallis, A. G. J. Am. Chem. Soc. 1994, 116, 7447. (m) Feldman, K. S.; Schildknegt, K. J Org. Chem. 1994, 59, 1129. (n) Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. (o) Zora, M.; Herndon, J. W. J. Org. Chem. 1994, 59, 699. (p) Liebeskind, L. S.; Bombrun, A. J. Org. Chem. 1994, 59, 1149 and referenced cited therein.
10. For reviews in this area, see: (a) The Total Synthesis of Natural Products ApSimon, J. W. Ed., John Wiley & Sons: New York: 1973; Vol. 1, p 81; 1973, Vol. 2, p 1, p 197, 1981, Vol. 4, p 353, p 451; 1983, Vol. 5, p 1; 1983, Vol. 7, p 275. (b) Mitra, A. The Synthesis of Prostaglandins; John Wiley & Sons: New York, 1977. (c) Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. (d) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer Verlag: Berlin, 1987. (e) Ramaiah, M. Synthesis 1984, 529. (f) Paquette, L. A. Top. Curr. Chem. 1984, 119, 1. (g) Curran, D. P. Synthesis 1988, 417, 489. (h) Shore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 1037. For some recent studies on this area, see: (i) Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. (j) Negishi, E.; Jensen, M. D.; Kondakov, D. Y.; Wang, S. J. Am. Chem. Soc. 1994, 116, 8404. (k) Lee, B. Y.; Chung, Y. K. J. Am Chem. Soc. 1994, 116, 8793. (l) Sturino, C. F.; Fallis, A. G. J. Am. Chem. Soc. 1994, 116, 7447. (m) Feldman, K. S.; Schildknegt, K. J Org. Chem. 1994, 59, 1129. (n) Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. (o) Zora, M.; Herndon, J. W. J. Org. Chem. 1994, 59, 699. (p) Liebeskind, L. S.; Bombrun, A. J. Org. Chem. 1994, 59, 1149 and referenced cited therein.
11. For reviews in this area, see: (a) The Total Synthesis of Natural Products ApSimon, J. W. Ed., John Wiley & Sons: New York: 1973; Vol. 1, p 81; 1973, Vol. 2, p 1, p 197, 1981, Vol. 4, p 353, p 451; 1983, Vol. 5, p 1; 1983, Vol. 7, p 275. (b) Mitra, A. The Synthesis of Prostaglandins; John Wiley & Sons: New York, 1977. (c) Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. (d) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer Verlag: Berlin, 1987. (e) Ramaiah, M. Synthesis 1984, 529. (f) Paquette, L. A. Top. Curr. Chem. 1984, 119, 1. (g) Curran, D. P. Synthesis 1988, 417, 489. (h) Shore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 1037. For some recent studies on this area, see: (i) Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. (j) Negishi, E.; Jensen, M. D.; Kondakov, D. Y.; Wang, S. J. Am. Chem. Soc. 1994, 116, 8404. (k) Lee, B. Y.; Chung, Y. K. J. Am Chem. Soc. 1994, 116, 8793. (l) Sturino, C. F.; Fallis, A. G. J. Am. Chem. Soc. 1994, 116, 7447. (m) Feldman, K. S.; Schildknegt, K. J Org. Chem. 1994, 59, 1129. (n) Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. (o) Zora, M.; Herndon, J. W. J. Org. Chem. 1994, 59, 699. (p) Liebeskind, L. S.; Bombrun, A. J. Org. Chem. 1994, 59, 1149 and referenced cited therein.
12. For reviews in this area, see: (a) The Total Synthesis of Natural Products ApSimon, J. W. Ed., John Wiley & Sons: New York: 1973; Vol. 1, p 81; 1973, Vol. 2, p 1, p 197, 1981, Vol. 4, p 353, p 451; 1983, Vol. 5, p 1; 1983, Vol. 7, p 275. (b) Mitra, A. The Synthesis of Prostaglandins; John Wiley & Sons: New York, 1977. (c) Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. (d) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer Verlag: Berlin, 1987. (e) Ramaiah, M. Synthesis 1984, 529. (f) Paquette, L. A. Top. Curr. Chem. 1984, 119, 1. (g) Curran, D. P. Synthesis 1988, 417, 489. (h) Shore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 1037. For some recent studies on this area, see: (i) Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. (j) Negishi, E.; Jensen, M. D.; Kondakov, D. Y.; Wang, S. J. Am. Chem. Soc. 1994, 116, 8404. (k) Lee, B. Y.; Chung, Y. K. J. Am Chem. Soc. 1994, 116, 8793. (l) Sturino, C. F.; Fallis, A. G. J. Am. Chem. Soc. 1994, 116, 7447. (m) Feldman, K. S.; Schildknegt, K. J Org. Chem. 1994, 59, 1129. (n) Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. (o) Zora, M.; Herndon, J. W. J. Org. Chem. 1994, 59, 699. (p) Liebeskind, L. S.; Bombrun, A. J. Org. Chem. 1994, 59, 1149 and referenced cited therein.
13. For reviews in this area, see: (a) The Total Synthesis of Natural Products ApSimon, J. W. Ed., John Wiley & Sons: New York: 1973; Vol. 1, p 81; 1973, Vol. 2, p 1, p 197, 1981, Vol. 4, p 353, p 451; 1983, Vol. 5, p 1; 1983, Vol. 7, p 275. (b) Mitra, A. The Synthesis of Prostaglandins; John Wiley & Sons: New York, 1977. (c) Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. (d) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer Verlag: Berlin, 1987. (e) Ramaiah, M. Synthesis 1984, 529. (f) Paquette, L. A. Top. Curr. Chem. 1984, 119, 1. (g) Curran, D. P. Synthesis 1988, 417, 489. (h) Shore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 1037. For some recent studies on this area, see: (i) Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. (j) Negishi, E.; Jensen, M. D.; Kondakov, D. Y.; Wang, S. J. Am. Chem. Soc. 1994, 116, 8404. (k) Lee, B. Y.; Chung, Y. K. J. Am Chem. Soc. 1994, 116, 8793. (l) Sturino, C. F.; Fallis, A. G. J. Am. Chem. Soc. 1994, 116, 7447. (m) Feldman, K. S.; Schildknegt, K. J Org. Chem. 1994, 59, 1129. (n) Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. (o) Zora, M.; Herndon, J. W. J. Org. Chem. 1994, 59, 699. (p) Liebeskind, L. S.; Bombrun, A. J. Org. Chem. 1994, 59, 1149 and referenced cited therein.
14. For reviews in this area, see: (a) The Total Synthesis of Natural Products ApSimon, J. W. Ed., John Wiley & Sons: New York: 1973; Vol. 1, p 81; 1973, Vol. 2, p 1, p 197, 1981, Vol. 4, p 353, p 451; 1983, Vol. 5, p 1; 1983, Vol. 7, p 275. (b) Mitra, A. The Synthesis of Prostaglandins; John Wiley & Sons: New York, 1977. (c) Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. (d) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer Verlag: Berlin, 1987. (e) Ramaiah, M. Synthesis 1984, 529. (f) Paquette, L. A. Top. Curr. Chem. 1984, 119, 1. (g) Curran, D. P. Synthesis 1988, 417, 489. (h) Shore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 1037. For some recent studies on this area, see: (i) Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. (j) Negishi, E.; Jensen, M. D.; Kondakov, D. Y.; Wang, S. J. Am. Chem. Soc. 1994, 116, 8404. (k) Lee, B. Y.; Chung, Y. K. J. Am Chem. Soc. 1994, 116, 8793. (l) Sturino, C. F.; Fallis, A. G. J. Am. Chem. Soc. 1994, 116, 7447. (m) Feldman, K. S.; Schildknegt, K. J Org. Chem. 1994, 59, 1129. (n) Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. (o) Zora, M.; Herndon, J. W. J. Org. Chem. 1994, 59, 699. (p) Liebeskind, L. S.; Bombrun, A. J. Org. Chem. 1994, 59, 1149 and referenced cited therein.
15. For reviews in this area, see: (a) The Total Synthesis of Natural Products ApSimon, J. W. Ed., John Wiley & Sons: New York: 1973; Vol. 1, p 81; 1973, Vol. 2, p 1, p 197, 1981, Vol. 4, p 353, p 451; 1983, Vol. 5, p 1; 1983, Vol. 7, p 275. (b) Mitra, A. The Synthesis of Prostaglandins; John Wiley & Sons: New York, 1977. (c) Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. (d) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer Verlag: Berlin, 1987. (e) Ramaiah, M. Synthesis 1984, 529. (f) Paquette, L. A. Top. Curr. Chem. 1984, 119, 1. (g) Curran, D. P. Synthesis 1988, 417, 489. (h) Shore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 1037. For some recent studies on this area, see: (i) Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. (j) Negishi, E.; Jensen, M. D.; Kondakov, D. Y.; Wang, S. J. Am. Chem. Soc. 1994, 116, 8404. (k) Lee, B. Y.; Chung, Y. K. J. Am Chem. Soc. 1994, 116, 8793. (l) Sturino, C. F.; Fallis, A. G. J. Am. Chem. Soc. 1994, 116, 7447. (m) Feldman, K. S.; Schildknegt, K. J Org. Chem. 1994, 59, 1129. (n) Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. (o) Zora, M.; Herndon, J. W. J. Org. Chem. 1994, 59, 699. (p) Liebeskind, L. S.; Bombrun, A. J. Org. Chem. 1994, 59, 1149 and referenced cited therein.
16. For reviews in this area, see: (a) The Total Synthesis of Natural Products ApSimon, J. W. Ed., John Wiley & Sons: New York: 1973; Vol. 1, p 81; 1973, Vol. 2, p 1, p 197, 1981, Vol. 4, p 353, p 451; 1983, Vol. 5, p 1; 1983, Vol. 7, p 275. (b) Mitra, A. The Synthesis of Prostaglandins; John Wiley & Sons: New York, 1977. (c) Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. (d) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer Verlag: Berlin, 1987. (e) Ramaiah, M. Synthesis 1984, 529. (f) Paquette, L. A. Top. Curr. Chem. 1984, 119, 1. (g) Curran, D. P. Synthesis 1988, 417, 489. (h) Shore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 1037. For some recent studies on this area, see: (i) Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. (j) Negishi, E.; Jensen, M. D.; Kondakov, D. Y.; Wang, S. J. Am. Chem. Soc. 1994, 116, 8404. (k) Lee, B. Y.; Chung, Y. K. J. Am Chem. Soc. 1994, 116, 8793. (l) Sturino, C. F.; Fallis, A. G. J. Am. Chem. Soc. 1994, 116, 7447. (m) Feldman, K. S.; Schildknegt, K. J Org. Chem. 1994, 59, 1129. (n) Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. (o) Zora, M.; Herndon, J. W. J. Org. Chem. 1994, 59, 699. (p) Liebeskind, L. S.; Bombrun, A. J. Org. Chem. 1994, 59, 1149 and referenced cited therein.
17. For reviews in this area, see: (a) The Total Synthesis of Natural Products ApSimon, J. W. Ed., John Wiley & Sons: New York: 1973; Vol. 1, p 81; 1973, Vol. 2, p 1, p 197, 1981, Vol. 4, p 353, p 451; 1983, Vol. 5, p 1; 1983, Vol. 7, p 275. (b) Mitra, A. The Synthesis of Prostaglandins; John Wiley & Sons: New York, 1977. (c) Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. (d) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer Verlag: Berlin, 1987. (e) Ramaiah, M. Synthesis 1984, 529. (f) Paquette, L. A. Top. Curr. Chem. 1984, 119, 1. (g) Curran, D. P. Synthesis 1988, 417, 489. (h) Shore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 1037. For some recent studies on this area, see: (i) Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. (j) Negishi, E.; Jensen, M. D.; Kondakov, D. Y.; Wang, S. J. Am. Chem. Soc. 1994, 116, 8404. (k) Lee, B. Y.; Chung, Y. K. J. Am Chem. Soc. 1994, 116, 8793. (l) Sturino, C. F.; Fallis, A. G. J. Am. Chem. Soc. 1994, 116, 7447. (m) Feldman, K. S.; Schildknegt, K. J Org. Chem. 1994, 59, 1129. (n) Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. (o) Zora, M.; Herndon, J. W. J. Org. Chem. 1994, 59, 699. (p) Liebeskind, L. S.; Bombrun, A. J. Org. Chem. 1994, 59, 1149 and referenced cited therein.
18. For reviews in this area, see: (a) The Total Synthesis of Natural Products ApSimon, J. W. Ed., John Wiley & Sons: New York: 1973; Vol. 1, p 81; 1973, Vol. 2, p 1, p 197, 1981, Vol. 4, p 353, p 451; 1983, Vol. 5, p 1; 1983, Vol. 7, p 275. (b) Mitra, A. The Synthesis of Prostaglandins; John Wiley & Sons: New York, 1977. (c) Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. (d) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer Verlag: Berlin, 1987. (e) Ramaiah, M. Synthesis 1984, 529. (f) Paquette, L. A. Top. Curr. Chem. 1984, 119, 1. (g) Curran, D. P. Synthesis 1988, 417, 489. (h) Shore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 1037. For some recent studies on this area, see: (i) Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. (j) Negishi, E.; Jensen, M. D.; Kondakov, D. Y.; Wang, S. J. Am. Chem. Soc. 1994, 116, 8404. (k) Lee, B. Y.; Chung, Y. K. J. Am Chem. Soc. 1994, 116, 8793. (l) Sturino, C. F.; Fallis, A. G. J. Am. Chem. Soc. 1994, 116, 7447. (m) Feldman, K. S.; Schildknegt, K. J Org. Chem. 1994, 59, 1129. (n) Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. (o) Zora, M.; Herndon, J. W. J. Org. Chem. 1994, 59, 699. (p) Liebeskind, L. S.; Bombrun, A. J. Org. Chem. 1994, 59, 1149 and referenced cited therein.
19. For reviews in this area, see: (a) The Total Synthesis of Natural Products ApSimon, J. W. Ed., John Wiley & Sons: New York: 1973; Vol. 1, p 81; 1973, Vol. 2, p 1, p 197, 1981, Vol. 4, p 353, p 451; 1983, Vol. 5, p 1; 1983, Vol. 7, p 275. (b) Mitra, A. The Synthesis of Prostaglandins; John Wiley & Sons: New York, 1977. (c) Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. (d) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer Verlag: Berlin, 1987. (e) Ramaiah, M. Synthesis 1984, 529. (f) Paquette, L. A. Top. Curr. Chem. 1984, 119, 1. (g) Curran, D. P. Synthesis 1988, 417, 489. (h) Shore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 1037. For some recent studies on this area, see: (i) Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. (j) Negishi, E.; Jensen, M. D.; Kondakov, D. Y.; Wang, S. J. Am. Chem. Soc. 1994, 116, 8404. (k) Lee, B. Y.; Chung, Y. K. J. Am Chem. Soc. 1994, 116, 8793. (l) Sturino, C. F.; Fallis, A. G. J. Am. Chem. Soc. 1994, 116, 7447. (m) Feldman, K. S.; Schildknegt, K. J Org. Chem. 1994, 59, 1129. (n) Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. (o) Zora, M.; Herndon, J. W. J. Org. Chem. 1994, 59, 699. (p) Liebeskind, L. S.; Bombrun, A. J. Org. Chem. 1994, 59, 1149 and referenced cited therein.
20. For reviews in this area, see: (a) The Total Synthesis of Natural Products ApSimon, J. W. Ed., John Wiley & Sons: New York: 1973; Vol. 1, p 81; 1973, Vol. 2, p 1, p 197, 1981, Vol. 4, p 353, p 451; 1983, Vol. 5, p 1; 1983, Vol. 7, p 275. (b) Mitra, A. The Synthesis of Prostaglandins; John Wiley & Sons: New York, 1977. (c) Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. (d) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer Verlag: Berlin, 1987. (e) Ramaiah, M. Synthesis 1984, 529. (f) Paquette, L. A. Top. Curr. Chem. 1984, 119, 1. (g) Curran, D. P. Synthesis 1988, 417, 489. (h) Shore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 1037. For some recent studies on this area, see: (i) Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. (j) Negishi, E.; Jensen, M. D.; Kondakov, D. Y.; Wang, S. J. Am. Chem. Soc. 1994, 116, 8404. (k) Lee, B. Y.; Chung, Y. K. J. Am Chem. Soc. 1994, 116, 8793. (l) Sturino, C. F.; Fallis, A. G. J. Am. Chem. Soc. 1994, 116, 7447. (m) Feldman, K. S.; Schildknegt, K. J Org. Chem. 1994, 59, 1129. (n) Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. (o) Zora, M.; Herndon, J. W. J. Org. Chem. 1994, 59, 699. (p) Liebeskind, L. S.; Bombrun, A. J. Org. Chem. 1994, 59, 1149 and referenced cited therein.
21. For reviews in this area, see: (a) The Total Synthesis of Natural Products ApSimon, J. W. Ed., John Wiley & Sons: New York: 1973; Vol. 1, p 81; 1973, Vol. 2, p 1, p 197, 1981, Vol. 4, p 353, p 451; 1983, Vol. 5, p 1; 1983, Vol. 7, p 275. (b) Mitra, A. The Synthesis of Prostaglandins; John Wiley & Sons: New York, 1977. (c) Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. (d) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer Verlag: Berlin, 1987. (e) Ramaiah, M. Synthesis 1984, 529. (f) Paquette, L. A. Top. Curr. Chem. 1984, 119, 1. (g) Curran, D. P. Synthesis 1988, 417, 489. (h) Shore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 1037. For some recent studies on this area, see: (i) Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. (j) Negishi, E.; Jensen, M. D.; Kondakov, D. Y.; Wang, S. J. Am. Chem. Soc. 1994, 116, 8404. (k) Lee, B. Y.; Chung, Y. K. J. Am Chem. Soc. 1994, 116, 8793. (l) Sturino, C. F.; Fallis, A. G. J. Am. Chem. Soc. 1994, 116, 7447. (m) Feldman, K. S.; Schildknegt, K. J Org. Chem. 1994, 59, 1129. (n) Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. (o) Zora, M.; Herndon, J. W. J. Org. Chem. 1994, 59, 699. (p) Liebeskind, L. S.; Bombrun, A. J. Org. Chem. 1994, 59, 1149 and referenced cited therein.
22. For reviews in this area, see: (a) The Total Synthesis of Natural Products ApSimon, J. W. Ed., John Wiley & Sons: New York: 1973; Vol. 1, p 81; 1973, Vol. 2, p 1, p 197, 1981, Vol. 4, p 353, p 451; 1983, Vol. 5, p 1; 1983, Vol. 7, p 275. (b) Mitra, A. The Synthesis of Prostaglandins; John Wiley & Sons: New York, 1977. (c) Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. (d) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer Verlag: Berlin, 1987. (e) Ramaiah, M. Synthesis 1984, 529. (f) Paquette, L. A. Top. Curr. Chem. 1984, 119, 1. (g) Curran, D. P. Synthesis 1988, 417, 489. (h) Shore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 1037. For some recent studies on this area, see: (i) Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. (j) Negishi, E.; Jensen, M. D.; Kondakov, D. Y.; Wang, S. J. Am. Chem. Soc. 1994, 116, 8404. (k) Lee, B. Y.; Chung, Y. K. J. Am Chem. Soc. 1994, 116, 8793. (l) Sturino, C. F.; Fallis, A. G. J. Am. Chem. Soc. 1994, 116, 7447. (m) Feldman, K. S.; Schildknegt, K. J Org. Chem. 1994, 59, 1129. (n) Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. (o) Zora, M.; Herndon, J. W. J. Org. Chem. 1994, 59, 699. (p) Liebeskind, L. S.; Bombrun, A. J. Org. Chem. 1994, 59, 1149 and referenced cited therein.
23. For reviews in this area, see: (a) The Total Synthesis of Natural Products ApSimon, J. W. Ed., John Wiley & Sons: New York: 1973; Vol. 1, p 81; 1973, Vol. 2, p 1, p 197, 1981, Vol. 4, p 353, p 451; 1983, Vol. 5, p 1; 1983, Vol. 7, p 275. (b) Mitra, A. The Synthesis of Prostaglandins; John Wiley & Sons: New York, 1977. (c) Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. (d) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer Verlag: Berlin, 1987. (e) Ramaiah, M. Synthesis 1984, 529. (f) Paquette, L. A. Top. Curr. Chem. 1984, 119, 1. (g) Curran, D. P. Synthesis 1988, 417, 489. (h) Shore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 1037. For some recent studies on this area, see: (i) Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. (j) Negishi, E.; Jensen, M. D.; Kondakov, D. Y.; Wang, S. J. Am. Chem. Soc. 1994, 116, 8404. (k) Lee, B. Y.; Chung, Y. K. J. Am Chem. Soc. 1994, 116, 8793. (l) Sturino, C. F.; Fallis, A. G. J. Am. Chem. Soc. 1994, 116, 7447. (m) Feldman, K. S.; Schildknegt, K. J Org. Chem. 1994, 59, 1129. (n) Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. (o) Zora, M.; Herndon, J. W. J. Org. Chem. 1994, 59, 699. (p) Liebeskind, L. S.; Bombrun, A. J. Org. Chem. 1994, 59, 1149 and referenced cited therein.
24. For reviews in this area, see: (a) The Total Synthesis of Natural Products ApSimon, J. W. Ed., John Wiley & Sons: New York: 1973; Vol. 1, p 81; 1973, Vol. 2, p 1, p 197, 1981, Vol. 4, p 353, p 451; 1983, Vol. 5, p 1; 1983, Vol. 7, p 275. (b) Mitra, A. The Synthesis of Prostaglandins; John Wiley & Sons: New York, 1977. (c) Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. (d) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer Verlag: Berlin, 1987. (e) Ramaiah, M. Synthesis 1984, 529. (f) Paquette, L. A. Top. Curr. Chem. 1984, 119, 1. (g) Curran, D. P. Synthesis 1988, 417, 489. (h) Shore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 1037. For some recent studies on this area, see: (i) Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. (j) Negishi, E.; Jensen, M. D.; Kondakov, D. Y.; Wang, S. J. Am. Chem. Soc. 1994, 116, 8404. (k) Lee, B. Y.; Chung, Y. K. J. Am Chem. Soc. 1994, 116, 8793. (l) Sturino, C. F.; Fallis, A. G. J. Am. Chem. Soc. 1994, 116, 7447. (m) Feldman, K. S.; Schildknegt, K. J Org. Chem. 1994, 59, 1129. (n) Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. (o) Zora, M.; Herndon, J. W. J. Org. Chem. 1994, 59, 699. (p) Liebeskind, L. S.; Bombrun, A. J. Org. Chem. 1994, 59, 1149 and referenced cited therein.
25. For reviews in this area, see: (a) The Total Synthesis of Natural Products ApSimon, J. W. Ed., John Wiley & Sons: New York: 1973; Vol. 1, p 81; 1973, Vol. 2, p 1, p 197, 1981, Vol. 4, p 353, p 451; 1983, Vol. 5, p 1; 1983, Vol. 7, p 275. (b) Mitra, A. The Synthesis of Prostaglandins; John Wiley & Sons: New York, 1977. (c) Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. (d) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer Verlag: Berlin, 1987. (e) Ramaiah, M. Synthesis 1984, 529. (f) Paquette, L. A. Top. Curr. Chem. 1984, 119, 1. (g) Curran, D. P. Synthesis 1988, 417, 489. (h) Shore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 1037. For some recent studies on this area, see: (i) Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. (j) Negishi, E.; Jensen, M. D.; Kondakov, D. Y.; Wang, S. J. Am. Chem. Soc. 1994, 116, 8404. (k) Lee, B. Y.; Chung, Y. K. J. Am Chem. Soc. 1994, 116, 8793. (l) Sturino, C. F.; Fallis, A. G. J. Am. Chem. Soc. 1994, 116, 7447. (m) Feldman, K. S.; Schildknegt, K. J Org. Chem. 1994, 59, 1129. (n) Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. (o) Zora, M.; Herndon, J. W. J. Org. Chem. 1994, 59, 699. (p) Liebeskind, L. S.; Bombrun, A. J. Org. Chem. 1994, 59, 1149 and referenced cited therein.
26. For reviews in this area, see: (a) The Total Synthesis of Natural Products ApSimon, J. W. Ed., John Wiley & Sons: New York: 1973; Vol. 1, p 81; 1973, Vol. 2, p 1, p 197, 1981, Vol. 4, p 353, p 451; 1983, Vol. 5, p 1; 1983, Vol. 7, p 275. (b) Mitra, A. The Synthesis of Prostaglandins; John Wiley & Sons: New York, 1977. (c) Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. (d) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer Verlag: Berlin, 1987. (e) Ramaiah, M. Synthesis 1984, 529. (f) Paquette, L. A. Top. Curr. Chem. 1984, 119, 1. (g) Curran, D. P. Synthesis 1988, 417, 489. (h) Shore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 1037. For some recent studies on this area, see: (i) Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. (j) Negishi, E.; Jensen, M. D.; Kondakov, D. Y.; Wang, S. J. Am. Chem. Soc. 1994, 116, 8404. (k) Lee, B. Y.; Chung, Y. K. J. Am Chem. Soc. 1994, 116, 8793. (l) Sturino, C. F.; Fallis, A. G. J. Am. Chem. Soc. 1994, 116, 7447. (m) Feldman, K. S.; Schildknegt, K. J Org. Chem. 1994, 59, 1129. (n) Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. (o) Zora, M.; Herndon, J. W. J. Org. Chem. 1994, 59, 699. (p) Liebeskind, L. S.; Bombrun, A. J. Org. Chem. 1994, 59, 1149 and referenced cited therein.
27. For reviews in this area, see: (a) The Total Synthesis of Natural Products ApSimon, J. W. Ed., John Wiley & Sons: New York: 1973; Vol. 1, p 81; 1973, Vol. 2, p 1, p 197, 1981, Vol. 4, p 353, p 451; 1983, Vol. 5, p 1; 1983, Vol. 7, p 275. (b) Mitra, A. The Synthesis of Prostaglandins; John Wiley & Sons: New York, 1977. (c) Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. (d) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer Verlag: Berlin, 1987. (e) Ramaiah, M. Synthesis 1984, 529. (f) Paquette, L. A. Top. Curr. Chem. 1984, 119, 1. (g) Curran, D. P. Synthesis 1988, 417, 489. (h) Shore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 1037. For some recent studies on this area, see: (i) Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. (j) Negishi, E.; Jensen, M. D.; Kondakov, D. Y.; Wang, S. J. Am. Chem. Soc. 1994, 116, 8404. (k) Lee, B. Y.; Chung, Y. K. J. Am Chem. Soc. 1994, 116, 8793. (l) Sturino, C. F.; Fallis, A. G. J. Am. Chem. Soc. 1994, 116, 7447. (m) Feldman, K. S.; Schildknegt, K. J Org. Chem. 1994, 59, 1129. (n) Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. (o) Zora, M.; Herndon, J. W. J. Org. Chem. 1994, 59, 699. (p) Liebeskind, L. S.; Bombrun, A. J. Org. Chem. 1994, 59, 1149 and referenced cited therein.
28. For reviews in this area, see: (a) The Total Synthesis of Natural Products ApSimon, J. W. Ed., John Wiley & Sons: New York: 1973; Vol. 1, p 81; 1973, Vol. 2, p 1, p 197, 1981, Vol. 4, p 353, p 451; 1983, Vol. 5, p 1; 1983, Vol. 7, p 275. (b) Mitra, A. The Synthesis of Prostaglandins; John Wiley & Sons: New York, 1977. (c) Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. (d) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer Verlag: Berlin, 1987. (e) Ramaiah, M. Synthesis 1984, 529. (f) Paquette, L. A. Top. Curr. Chem. 1984, 119, 1. (g) Curran, D. P. Synthesis 1988, 417, 489. (h) Shore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 1037. For some recent studies on this area, see: (i) Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. (j) Negishi, E.; Jensen, M. D.; Kondakov, D. Y.; Wang, S. J. Am. Chem. Soc. 1994, 116, 8404. (k) Lee, B. Y.; Chung, Y. K. J. Am Chem. Soc. 1994, 116, 8793. (l) Sturino, C. F.; Fallis, A. G. J. Am. Chem. Soc. 1994, 116, 7447. (m) Feldman, K. S.; Schildknegt, K. J Org. Chem. 1994, 59, 1129. (n) Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. (o) Zora, M.; Herndon, J. W. J. Org. Chem. 1994, 59, 699. (p) Liebeskind, L. S.; Bombrun, A. J. Org. Chem. 1994, 59, 1149 and referenced cited therein.
29. For reviews in this area, see: (a) Gilman, H.; Jones, R. G. Org. React. (N.Y.) 1951, 6, 339. (b) Sheverdina, N. T.; Kocheshkov, K. A. In The Organic Compounds of Zinc and Cadmium in Methods of Element-Organic Chemistry; Newsmeyanov, A. N.; Kocheshkov, K. A., Eds., North-Holland Publishing Co.: Amsterdam, 1967. (d) Boersma, J. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 2, p 823. (e) Erdik, E. Tetrahedron 1987, 43, 2203. (f) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, p 211. (g) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49. (h) Niwa, S. Chem. Rev. 1992, 92, 833. (i) Erdik, E. Tetrahedron 1992, 48, 9577. (j) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117. For some recent studies in this area, see: (k) Bailey, W. F.; Punzalan, E. R. J. Org. Chem. 1990, 55, 5404. (l) Negishi, E.; Swanson, D. R.; Rousset, C. J. J. Org. Chem. 1990, 55, 5406. (m) Stadtmuller, H.; Lentz, R.; Tucker, C. E ; Studemann, T.; Dorner, W.; Knochel, P. J. Am. Chem. Soc. 1993, 115, 7027. (n) Gao, Y.; Urabe, H.; Sato, F. J. Org. Chem. 1994, 59, 5521 and references cited therein.
30. For reviews in this area, see: (a) Gilman, H.; Jones, R. G. Org. React. (N.Y.) 1951, 6, 339. (b) Sheverdina, N. T.; Kocheshkov, K. A. In The Organic Compounds of Zinc and Cadmium in Methods of Element-Organic Chemistry; Newsmeyanov, A. N.; Kocheshkov, K. A., Eds., North-Holland Publishing Co.: Amsterdam, 1967. (d) Boersma, J. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 2, p 823. (e) Erdik, E. Tetrahedron 1987, 43, 2203. (f) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, p 211. (g) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49. (h) Niwa, S. Chem. Rev. 1992, 92, 833. (i) Erdik, E. Tetrahedron 1992, 48, 9577. (j) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117. For some recent studies in this area, see: (k) Bailey, W. F.; Punzalan, E. R. J. Org. Chem. 1990, 55, 5404. (l) Negishi, E.; Swanson, D. R.; Rousset, C. J. J. Org. Chem. 1990, 55, 5406. (m) Stadtmuller, H.; Lentz, R.; Tucker, C. E ; Studemann, T.; Dorner, W.; Knochel, P. J. Am. Chem. Soc. 1993, 115, 7027. (n) Gao, Y.; Urabe, H.; Sato, F. J. Org. Chem. 1994, 59, 5521 and references cited therein.
31. For reviews in this area, see: (a) Gilman, H.; Jones, R. G. Org. React. (N.Y.) 1951, 6, 339. (b) Sheverdina, N. T.; Kocheshkov, K. A. In The Organic Compounds of Zinc and Cadmium in Methods of Element-Organic Chemistry; Newsmeyanov, A. N.; Kocheshkov, K. A., Eds., North-Holland Publishing Co.: Amsterdam, 1967. (d) Boersma, J. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 2, p 823. (e) Erdik, E. Tetrahedron 1987, 43, 2203. (f) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, p 211. (g) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49. (h) Niwa, S. Chem. Rev. 1992, 92, 833. (i) Erdik, E. Tetrahedron 1992, 48, 9577. (j) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117. For some recent studies in this area, see: (k) Bailey, W. F.; Punzalan, E. R. J. Org. Chem. 1990, 55, 5404. (l) Negishi, E.; Swanson, D. R.; Rousset, C. J. J. Org. Chem. 1990, 55, 5406. (m) Stadtmuller, H.; Lentz, R.; Tucker, C. E ; Studemann, T.; Dorner, W.; Knochel, P. J. Am. Chem. Soc. 1993, 115, 7027. (n) Gao, Y.; Urabe, H.; Sato, F. J. Org. Chem. 1994, 59, 5521 and references cited therein.
32. For reviews in this area, see: (a) Gilman, H.; Jones, R. G. Org. React. (N.Y.) 1951, 6, 339. (b) Sheverdina, N. T.; Kocheshkov, K. A. In The Organic Compounds of Zinc and Cadmium in Methods of Element-Organic Chemistry; Newsmeyanov, A. N.; Kocheshkov, K. A., Eds., North-Holland Publishing Co.: Amsterdam, 1967. (d) Boersma, J. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 2, p 823. (e) Erdik, E. Tetrahedron 1987, 43, 2203. (f) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, p 211. (g) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49. (h) Niwa, S. Chem. Rev. 1992, 92, 833. (i) Erdik, E. Tetrahedron 1992, 48, 9577. (j) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117. For some recent studies in this area, see: (k) Bailey, W. F.; Punzalan, E. R. J. Org. Chem. 1990, 55, 5404. (l) Negishi, E.; Swanson, D. R.; Rousset, C. J. J. Org. Chem. 1990, 55, 5406. (m) Stadtmuller, H.; Lentz, R.; Tucker, C. E ; Studemann, T.; Dorner, W.; Knochel, P. J. Am. Chem. Soc. 1993, 115, 7027. (n) Gao, Y.; Urabe, H.; Sato, F. J. Org. Chem. 1994, 59, 5521 and references cited therein.
33. For reviews in this area, see: (a) Gilman, H.; Jones, R. G. Org. React. (N.Y.) 1951, 6, 339. (b) Sheverdina, N. T.; Kocheshkov, K. A. In The Organic Compounds of Zinc and Cadmium in Methods of Element-Organic Chemistry; Newsmeyanov, A. N.; Kocheshkov, K. A., Eds., North-Holland Publishing Co.: Amsterdam, 1967. (d) Boersma, J. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 2, p 823. (e) Erdik, E. Tetrahedron 1987, 43, 2203. (f) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, p 211. (g) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49. (h) Niwa, S. Chem. Rev. 1992, 92, 833. (i) Erdik, E. Tetrahedron 1992, 48, 9577. (j) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117. For some recent studies in this area, see: (k) Bailey, W. F.; Punzalan, E. R. J. Org. Chem. 1990, 55, 5404. (l) Negishi, E.; Swanson, D. R.; Rousset, C. J. J. Org. Chem. 1990, 55, 5406. (m) Stadtmuller, H.; Lentz, R.; Tucker, C. E ; Studemann, T.; Dorner, W.; Knochel, P. J. Am. Chem. Soc. 1993, 115, 7027. (n) Gao, Y.; Urabe, H.; Sato, F. J. Org. Chem. 1994, 59, 5521 and references cited therein.
34. For reviews in this area, see: (a) Gilman, H.; Jones, R. G. Org. React. (N.Y.) 1951, 6, 339. (b) Sheverdina, N. T.; Kocheshkov, K. A. In The Organic Compounds of Zinc and Cadmium in Methods of Element-Organic Chemistry; Newsmeyanov, A. N.; Kocheshkov, K. A., Eds., North-Holland Publishing Co.: Amsterdam, 1967. (d) Boersma, J. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 2, p 823. (e) Erdik, E. Tetrahedron 1987, 43, 2203. (f) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, p 211. (g) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49. (h) Niwa, S. Chem. Rev. 1992, 92, 833. (i) Erdik, E. Tetrahedron 1992, 48, 9577. (j) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117. For some recent studies in this area, see: (k) Bailey, W. F.; Punzalan, E. R. J. Org. Chem. 1990, 55, 5404. (l) Negishi, E.; Swanson, D. R.; Rousset, C. J. J. Org. Chem. 1990, 55, 5406. (m) Stadtmuller, H.; Lentz, R.; Tucker, C. E ; Studemann, T.; Dorner, W.; Knochel, P. J. Am. Chem. Soc. 1993, 115, 7027. (n) Gao, Y.; Urabe, H.; Sato, F. J. Org. Chem. 1994, 59, 5521 and references cited therein.
35. For reviews in this area, see: (a) Gilman, H.; Jones, R. G. Org. React. (N.Y.) 1951, 6, 339. (b) Sheverdina, N. T.; Kocheshkov, K. A. In The Organic Compounds of Zinc and Cadmium in Methods of Element-Organic Chemistry; Newsmeyanov, A. N.; Kocheshkov, K. A., Eds., North-Holland Publishing Co.: Amsterdam, 1967. (d) Boersma, J. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 2, p 823. (e) Erdik, E. Tetrahedron 1987, 43, 2203. (f) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, p 211. (g) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49. (h) Niwa, S. Chem. Rev. 1992, 92, 833. (i) Erdik, E. Tetrahedron 1992, 48, 9577. (j) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117. For some recent studies in this area, see: (k) Bailey, W. F.; Punzalan, E. R. J. Org. Chem. 1990, 55, 5404. (l) Negishi, E.; Swanson, D. R.; Rousset, C. J. J. Org. Chem. 1990, 55, 5406. (m) Stadtmuller, H.; Lentz, R.; Tucker, C. E ; Studemann, T.; Dorner, W.; Knochel, P. J. Am. Chem. Soc. 1993, 115, 7027. (n) Gao, Y.; Urabe, H.; Sato, F. J. Org. Chem. 1994, 59, 5521 and references cited therein.
36. For reviews in this area, see: (a) Gilman, H.; Jones, R. G. Org. React. (N.Y.) 1951, 6, 339. (b) Sheverdina, N. T.; Kocheshkov, K. A. In The Organic Compounds of Zinc and Cadmium in Methods of Element-Organic Chemistry; Newsmeyanov, A. N.; Kocheshkov, K. A., Eds., North-Holland Publishing Co.: Amsterdam, 1967. (d) Boersma, J. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 2, p 823. (e) Erdik, E. Tetrahedron 1987, 43, 2203. (f) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, p 211. (g) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49. (h) Niwa, S. Chem. Rev. 1992, 92, 833. (i) Erdik, E. Tetrahedron 1992, 48, 9577. (j) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117. For some recent studies in this area, see: (k) Bailey, W. F.; Punzalan, E. R. J. Org. Chem. 1990, 55, 5404. (l) Negishi, E.; Swanson, D. R.; Rousset, C. J. J. Org. Chem. 1990, 55, 5406. (m) Stadtmuller, H.; Lentz, R.; Tucker, C. E ; Studemann, T.; Dorner, W.; Knochel, P. J. Am. Chem. Soc. 1993, 115, 7027. (n) Gao, Y.; Urabe, H.; Sato, F. J. Org. Chem. 1994, 59, 5521 and references cited therein.
37. For reviews in this area, see: (a) Gilman, H.; Jones, R. G. Org. React. (N.Y.) 1951, 6, 339. (b) Sheverdina, N. T.; Kocheshkov, K. A. In The Organic Compounds of Zinc and Cadmium in Methods of Element-Organic Chemistry; Newsmeyanov, A. N.; Kocheshkov, K. A., Eds., North-Holland Publishing Co.: Amsterdam, 1967. (d) Boersma, J. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 2, p 823. (e) Erdik, E. Tetrahedron 1987, 43, 2203. (f) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, p 211. (g) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49. (h) Niwa, S. Chem. Rev. 1992, 92, 833. (i) Erdik, E. Tetrahedron 1992, 48, 9577. (j) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117. For some recent studies in this area, see: (k) Bailey, W. F.; Punzalan, E. R. J. Org. Chem. 1990, 55, 5404. (l) Negishi, E.; Swanson, D. R.; Rousset, C. J. J. Org. Chem. 1990, 55, 5406. (m) Stadtmuller, H.; Lentz, R.; Tucker, C. E ; Studemann, T.; Dorner, W.; Knochel, P. J. Am. Chem. Soc. 1993, 115, 7027. (n) Gao, Y.; Urabe, H.; Sato, F. J. Org. Chem. 1994, 59, 5521 and references cited therein.
38. For reviews in this area, see: (a) Gilman, H.; Jones, R. G. Org. React. (N.Y.) 1951, 6, 339. (b) Sheverdina, N. T.; Kocheshkov, K. A. In The Organic Compounds of Zinc and Cadmium in Methods of Element-Organic Chemistry; Newsmeyanov, A. N.; Kocheshkov, K. A., Eds., North-Holland Publishing Co.: Amsterdam, 1967. (d) Boersma, J. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 2, p 823. (e) Erdik, E. Tetrahedron 1987, 43, 2203. (f) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, p 211. (g) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49. (h) Niwa, S. Chem. Rev. 1992, 92, 833. (i) Erdik, E. Tetrahedron 1992, 48, 9577. (j) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117. For some recent studies in this area, see: (k) Bailey, W. F.; Punzalan, E. R. J. Org. Chem. 1990, 55, 5404. (l) Negishi, E.; Swanson, D. R.; Rousset, C. J. J. Org. Chem. 1990, 55, 5406. (m) Stadtmuller, H.; Lentz, R.; Tucker, C. E ; Studemann, T.; Dorner, W.; Knochel, P. J. Am. Chem. Soc. 1993, 115, 7027. (n) Gao, Y.; Urabe, H.; Sato, F. J. Org. Chem. 1994, 59, 5521 and references cited therein.
39. For reviews in this area, see: (a) Gilman, H.; Jones, R. G. Org. React. (N.Y.) 1951, 6, 339. (b) Sheverdina, N. T.; Kocheshkov, K. A. In The Organic Compounds of Zinc and Cadmium in Methods of Element-Organic Chemistry; Newsmeyanov, A. N.; Kocheshkov, K. A., Eds., North-Holland Publishing Co.: Amsterdam, 1967. (d) Boersma, J. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 2, p 823. (e) Erdik, E. Tetrahedron 1987, 43, 2203. (f) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, p 211. (g) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49. (h) Niwa, S. Chem. Rev. 1992, 92, 833. (i) Erdik, E. Tetrahedron 1992, 48, 9577. (j) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117. For some recent studies in this area, see: (k) Bailey, W. F.; Punzalan, E. R. J. Org. Chem. 1990, 55, 5404. (l) Negishi, E.; Swanson, D. R.; Rousset, C. J. J. Org. Chem. 1990, 55, 5406. (m) Stadtmuller, H.; Lentz, R.; Tucker, C. E ; Studemann, T.; Dorner, W.; Knochel, P. J. Am. Chem. Soc. 1993, 115, 7027. (n) Gao, Y.; Urabe, H.; Sato, F. J. Org. Chem. 1994, 59, 5521 and references cited therein.
40. For reviews in this area, see: (a) Gilman, H.; Jones, R. G. Org. React. (N.Y.) 1951, 6, 339. (b) Sheverdina, N. T.; Kocheshkov, K. A. In The Organic Compounds of Zinc and Cadmium in Methods of Element-Organic Chemistry; Newsmeyanov, A. N.; Kocheshkov, K. A., Eds., North-Holland Publishing Co.: Amsterdam, 1967. (d) Boersma, J. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 2, p 823. (e) Erdik, E. Tetrahedron 1987, 43, 2203. (f) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, p 211. (g) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49. (h) Niwa, S. Chem. Rev. 1992, 92, 833. (i) Erdik, E. Tetrahedron 1992, 48, 9577. (j) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117. For some recent studies in this area, see: (k) Bailey, W. F.; Punzalan, E. R. J. Org. Chem. 1990, 55, 5404. (l) Negishi, E.; Swanson, D. R.; Rousset, C. J. J. Org. Chem. 1990, 55, 5406. (m) Stadtmuller, H.; Lentz, R.; Tucker, C. E ; Studemann, T.; Dorner, W.; Knochel, P. J. Am. Chem. Soc. 1993, 115, 7027. (n) Gao, Y.; Urabe, H.; Sato, F. J. Org. Chem. 1994, 59, 5521 and references cited therein.
41. For reviews in this area, see: (a) Gilman, H.; Jones, R. G. Org. React. (N.Y.) 1951, 6, 339. (b) Sheverdina, N. T.; Kocheshkov, K. A. In The Organic Compounds of Zinc and Cadmium in Methods of Element-Organic Chemistry; Newsmeyanov, A. N.; Kocheshkov, K. A., Eds., North-Holland Publishing Co.: Amsterdam, 1967. (d) Boersma, J. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 2, p 823. (e) Erdik, E. Tetrahedron 1987, 43, 2203. (f) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, p 211. (g) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49. (h) Niwa, S. Chem. Rev. 1992, 92, 833. (i) Erdik, E. Tetrahedron 1992, 48, 9577. (j) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117. For some recent studies in this area, see: (k) Bailey, W. F.; Punzalan, E. R. J. Org. Chem. 1990, 55, 5404. (l) Negishi, E.; Swanson, D. R.; Rousset, C. J. J. Org. Chem. 1990, 55, 5406. (m) Stadtmuller, H.; Lentz, R.; Tucker, C. E ; Studemann, T.; Dorner, W.; Knochel, P. J. Am. Chem. Soc. 1993, 115, 7027. (n) Gao, Y.; Urabe, H.; Sato, F. J. Org. Chem. 1994, 59, 5521 and references cited therein.
42. For reviews in this area, see: (a) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon Press: New York, 1986. (b) Curran, D. P. Synthesis 1988, 417 and 489. (c) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. (d) Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 24, 296. (e) Smadja, W. Synlett 1994, 1. For some recent studies in this area, see: (f) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. (g) Curran, D. P.; Qi, H.; DeMello, N. C.; Lin, C.-H. J. Am. Chem. Soc. 1994, 116, 8430 and references cited therein.
43. For reviews in this area, see: (a) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon Press: New York, 1986. (b) Curran, D. P. Synthesis 1988, 417 and 489. (c) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. (d) Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 24, 296. (e) Smadja, W. Synlett 1994, 1. For some recent studies in this area, see: (f) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. (g) Curran, D. P.; Qi, H.; DeMello, N. C.; Lin, C.-H. J. Am. Chem. Soc. 1994, 116, 8430 and references cited therein.
44. For reviews in this area, see: (a) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon Press: New York, 1986. (b) Curran, D. P. Synthesis 1988, 417 and 489. (c) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. (d) Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 24, 296. (e) Smadja, W. Synlett 1994, 1. For some recent studies in this area, see: (f) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. (g) Curran, D. P.; Qi, H.; DeMello, N. C.; Lin, C.-H. J. Am. Chem. Soc. 1994, 116, 8430 and references cited therein.
45. For reviews in this area, see: (a) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon Press: New York, 1986. (b) Curran, D. P. Synthesis 1988, 417 and 489. (c) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. (d) Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 24, 296. (e) Smadja, W. Synlett 1994, 1. For some recent studies in this area, see: (f) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. (g) Curran, D. P.; Qi, H.; DeMello, N. C.; Lin, C.-H. J. Am. Chem. Soc. 1994, 116, 8430 and references cited therein.
46. For reviews in this area, see: (a) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon Press: New York, 1986. (b) Curran, D. P. Synthesis 1988, 417 and 489. (c) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. (d) Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 24, 296. (e) Smadja, W. Synlett 1994, 1. For some recent studies in this area, see: (f) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. (g) Curran, D. P.; Qi, H.; DeMello, N. C.; Lin, C.-H. J. Am. Chem. Soc. 1994, 116, 8430 and references cited therein.
47. For reviews in this area, see: (a) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon Press: New York, 1986. (b) Curran, D. P. Synthesis 1988, 417 and 489. (c) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. (d) Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 24, 296. (e) Smadja, W. Synlett 1994, 1. For some recent studies in this area, see: (f) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. (g) Curran, D. P.; Qi, H.; DeMello, N. C.; Lin, C.-H. J. Am. Chem. Soc. 1994, 116, 8430 and references cited therein.
48. For reviews in this area, see: (a) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon Press: New York, 1986. (b) Curran, D. P. Synthesis 1988, 417 and 489. (c) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. (d) Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 24, 296. (e) Smadja, W. Synlett 1994, 1. For some recent studies in this area, see: (f) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. (g) Curran, D. P.; Qi, H.; DeMello, N. C.; Lin, C.-H. J. Am. Chem. Soc. 1994, 116, 8430 and references cited therein.
49. Stafford, J A.; McMurry, J. E. Tetrahedron Lett. 1988, 29, 2531.
50. Nemoto, H.; Nagamoehi, M.; Ishibashi, H.; Fukumoto, K. J. Org. Chem 1994, 59, 74.
51. 1H NMR (500 MHz) studies as follows. Namely, the definite NOE enhancement between methyl (Ha) (1.73 ppm) and hydrogen (Hb) (2.34-2.44 ppm) of 24 showed the isopropenyl group and hydrogen (Hb) to be cis. The observation of NOE between methyl (Ha) (1.77 ppm) and methylene (Hb and Hc) (3.36 and 3.52 ppm) of the siloxymethyl group of 22 confirmed these two groups to be cis. On the other hand, no such enhancement between methyl (Ha) (1.76 ppm) and methylene (Hb and Hc) (3.68 and 3.93 ppm) of 23 showed these two groups to be trans. The structure of 20 and 21 was deduced by the analogous reaction of 15 and 16 as for 14. equation presented
52. 1H NMR (500 MHz) studies of these pure samples as follows: an NOE enhancement between Ha and Hb (3.06 and 3.46 ppm) and Hc (1.22-1.33 ppm) of 33c and no such effect between Ha and Hb (3.07 and 3.19 ppm) and Hc (1.20-1.34 ppm) of 34c were observed, showing iodomethyl and side chain of 33c and 34c to be cis and trans, respectively. The definite NOE enhancement between Ha (1.06 ppm) and Hb (3.66 ppm) of 33d and between Ha (1.08 ppm) and Hb and Hc (3.64 and 3.69 ppm) of 33e confirmed that the methyl and siloxymethyl groups of these compounds were cis. equation presented
53. GMMX (version 1.0), Serena Software, P. O. Box 3076, Bloomington, IN.