Total synthesis and absolute configuration of (-)-anthoplalone

Journal of Organic Chemistry

Volumn 64, Issue 13, 1999, Pages 4893-4900

  Hanessian, Stephen ^a   Cantin, Louis David ^a   Andreotti, Daniele ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; ALKENE DERIVATIVE; ANTHOPLALONE; PHOSPHONIC ACID DERIVATIVE; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BINDING; CHEMICAL REACTION; CHEMICAL STRUCTURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033603498     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990302n     Document Type: Article

References (91)

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9. For leading references see: (a) Smith, A. B., III; Condon, S. M.; McCauley, J. A. Acc. Chem. Res. 1998, 31, 35-46. (b) Westwell, A. D.; Williams, J. M. J. In Preparation of Alkenes: A Practical Approach; Williams, J. M. J., Ed.; Oxford University Press: New York, 1996; Chapter 9. (c) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863- 927. (d) Faulkner, D. J. Synthesis 1971, 175-189. For recent applications of vinyl inflates: (e) Smith, A. B., III; Condon, S. M.; McCauley, J. A.; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. E., Jr. J. Am. Chem. Soc. 1997, 119, 947-961, and references cited. (f) Ritter, K. Synthesis 1993, 735-762. (g) McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1980, 21, 4313-4316. For examples of rearrangements: (h) Smith, A. B., III; Chen, S. S.-Y.; Nelson, F. C.; Reichert, J. M.; Salvatore, B. A. J. Am. Chem. Soc. 1995, 117, 12013-12014. (i) Overman, L. E.; Lin, N.- H. J. Org. Chem. 1985, 50, 3669-3670. (j) Wilson, S. R.; Price, M. F. J. Org. Chem. 1984, 49, 722-725. (k) Wakabayashi, N.; Waters, R. M.; Church, J. P. Tetrahedron Lett. 1969, 3253-3256. For the examples of phosphorus reagents: (l) Yue, X.; Li, Y. Synthesis 1996, 736-740. (m) Vedejs, E.; Cabaj, J.; Peterson, M. J. J. Org. Chem. 1993, 58, 6509- 6512. (n) Jones, T. K.; Mills, S. G.; Reamer, R. A.; Askin, D.; Desmond, R.; Volante, R. P.; Shinkai, I. J. Am. Chem. Soc. 1989, 111, 1157- 1159. (o) Schreiber, S. L.; Sammakia, T.; Uehling, D. E. J. Org. Chem. 1989, 54, 15-16. For the use of alkyne metalation strategies: (p) Wipf, P.; Smitrovich, J. H.; Moon, C.-W. J. Org. Chem. 1992, 57, 3178-3186. (q) Carr, D. B.; Schwartz, J. J. Am. Chem. Soc. 1979, 101, 3521-3531. (r) Ireland, R. E.; Wipf, P. J. Org. Chem. 1990, 55, 1425-1426. (s) Marfat, A.; McGuirk, P. R.; Helquist, P. J. Org. Chem. 1978, 44, 3888- 3901.
10. For leading references see: (a) Smith, A. B., III; Condon, S. M.; McCauley, J. A. Acc. Chem. Res. 1998, 31, 35-46. (b) Westwell, A. D.; Williams, J. M. J. In Preparation of Alkenes: A Practical Approach; Williams, J. M. J., Ed.; Oxford University Press: New York, 1996; Chapter 9. (c) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863-927. (d) Faulkner, D. J. Synthesis 1971, 175-189. For recent applications of vinyl inflates: (e) Smith, A. B., III; Condon, S. M.; McCauley, J. A.; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. E., Jr. J. Am. Chem. Soc. 1997, 119, 947-961, and references cited. (f) Ritter, K. Synthesis 1993, 735-762. (g) McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1980, 21, 4313-4316. For examples of rearrangements: (h) Smith, A. B., III; Chen, S. S.-Y.; Nelson, F. C.; Reichert, J. M.; Salvatore, B. A. J. Am. Chem. Soc. 1995, 117, 12013-12014. (i) Overman, L. E.; Lin, N.- H. J. Org. Chem. 1985, 50, 3669-3670. (j) Wilson, S. R.; Price, M. F. J. Org. Chem. 1984, 49, 722-725. (k) Wakabayashi, N.; Waters, R. M.; Church, J. P. Tetrahedron Lett. 1969, 3253-3256. For the examples of phosphorus reagents: (l) Yue, X.; Li, Y. Synthesis 1996, 736-740. (m) Vedejs, E.; Cabaj, J.; Peterson, M. J. J. Org. Chem. 1993, 58, 6509- 6512. (n) Jones, T. K.; Mills, S. G.; Reamer, R. A.; Askin, D.; Desmond, R.; Volante, R. P.; Shinkai, I. J. Am. Chem. Soc. 1989, 111, 1157- 1159. (o) Schreiber, S. L.; Sammakia, T.; Uehling, D. E. J. Org. Chem. 1989, 54, 15-16. For the use of alkyne metalation strategies: (p) Wipf, P.; Smitrovich, J. H.; Moon, C.-W. J. Org. Chem. 1992, 57, 3178-3186. (q) Carr, D. B.; Schwartz, J. J. Am. Chem. Soc. 1979, 101, 3521-3531. (r) Ireland, R. E.; Wipf, P. J. Org. Chem. 1990, 55, 1425-1426. (s) Marfat, A.; McGuirk, P. R.; Helquist, P. J. Org. Chem. 1978, 44, 3888- 3901.
11. For leading references see: (a) Smith, A. B., III; Condon, S. M.; McCauley, J. A. Acc. Chem. Res. 1998, 31, 35-46. (b) Westwell, A. D.; Williams, J. M. J. In Preparation of Alkenes: A Practical Approach; Williams, J. M. J., Ed.; Oxford University Press: New York, 1996; Chapter 9. (c) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863- 927. (d) Faulkner, D. J. Synthesis 1971, 175-189. For recent applications of vinyl inflates: (e) Smith, A. B., III; Condon, S. M.; McCauley, J. A.; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. E., Jr. J. Am. Chem. Soc. 1997, 119, 947-961, and references cited. (f) Ritter, K. Synthesis 1993, 735-762. (g) McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1980, 21, 4313-4316. For examples of rearrangements: (h) Smith, A. B., III; Chen, S. S.-Y.; Nelson, F. C.; Reichert, J. M.; Salvatore, B. A. J. Am. Chem. Soc. 1995, 117, 12013-12014. (i) Overman, L. E.; Lin, N.- H. J. Org. Chem. 1985, 50, 3669-3670. (j) Wilson, S. R.; Price, M. F. J. Org. Chem. 1984, 49, 722-725. (k) Wakabayashi, N.; Waters, R. M.; Church, J. P. Tetrahedron Lett. 1969, 3253-3256. For the examples of phosphorus reagents: (l) Yue, X.; Li, Y. Synthesis 1996, 736-740. (m) Vedejs, E.; Cabaj, J.; Peterson, M. J. J. Org. Chem. 1993, 58, 6509- 6512. (n) Jones, T. K.; Mills, S. G.; Reamer, R. A.; Askin, D.; Desmond, R.; Volante, R. P.; Shinkai, I. J. Am. Chem. Soc. 1989, 111, 1157- 1159. (o) Schreiber, S. L.; Sammakia, T.; Uehling, D. E. J. Org. Chem. 1989, 54, 15-16. For the use of alkyne metalation strategies: (p) Wipf, P.; Smitrovich, J. H.; Moon, C.-W. J. Org. Chem. 1992, 57, 3178-3186. (q) Carr, D. B.; Schwartz, J. J. Am. Chem. Soc. 1979, 101, 3521-3531. (r) Ireland, R. E.; Wipf, P. J. Org. Chem. 1990, 55, 1425-1426. (s) Marfat, A.; McGuirk, P. R.; Helquist, P. J. Org. Chem. 1978, 44, 3888- 3901.
12. For leading references see: (a) Smith, A. B., III; Condon, S. M.; McCauley, J. A. Acc. Chem. Res. 1998, 31, 35-46. (b) Westwell, A. D.; Williams, J. M. J. In Preparation of Alkenes: A Practical Approach; Williams, J. M. J., Ed.; Oxford University Press: New York, 1996; Chapter 9. (c) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863- 927. (d) Faulkner, D. J. Synthesis 1971, 175-189. For recent applications of vinyl inflates: (e) Smith, A. B., III; Condon, S. M.; McCauley, J. A.; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. E., Jr. J. Am. Chem. Soc. 1997, 119, 947-961, and references cited. (f) Ritter, K. Synthesis 1993, 735-762. (g) McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1980, 21, 4313-4316. For examples of rearrangements: (h) Smith, A. B., III; Chen, S. S.-Y.; Nelson, F. C.; Reichert, J. M.; Salvatore, B. A. J. Am. Chem. Soc. 1995, 117, 12013-12014. (i) Overman, L. E.; Lin, N.- H. J. Org. Chem. 1985, 50, 3669-3670. (j) Wilson, S. R.; Price, M. F. J. Org. Chem. 1984, 49, 722-725. (k) Wakabayashi, N.; Waters, R. M.; Church, J. P. Tetrahedron Lett. 1969, 3253-3256. For the examples of phosphorus reagents: (l) Yue, X.; Li, Y. Synthesis 1996, 736-740. (m) Vedejs, E.; Cabaj, J.; Peterson, M. J. J. Org. Chem. 1993, 58, 6509- 6512. (n) Jones, T. K.; Mills, S. G.; Reamer, R. A.; Askin, D.; Desmond, R.; Volante, R. P.; Shinkai, I. J. Am. Chem. Soc. 1989, 111, 1157- 1159. (o) Schreiber, S. L.; Sammakia, T.; Uehling, D. E. J. Org. Chem. 1989, 54, 15-16. For the use of alkyne metalation strategies: (p) Wipf, P.; Smitrovich, J. H.; Moon, C.-W. J. Org. Chem. 1992, 57, 3178-3186. (q) Carr, D. B.; Schwartz, J. J. Am. Chem. Soc. 1979, 101, 3521-3531. (r) Ireland, R. E.; Wipf, P. J. Org. Chem. 1990, 55, 1425-1426. (s) Marfat, A.; McGuirk, P. R.; Helquist, P. J. Org. Chem. 1978, 44, 3888- 3901.
13. For leading references see: (a) Smith, A. B., III; Condon, S. M.; McCauley, J. A. Acc. Chem. Res. 1998, 31, 35-46. (b) Westwell, A. D.; Williams, J. M. J. In Preparation of Alkenes: A Practical Approach; Williams, J. M. J., Ed.; Oxford University Press: New York, 1996; Chapter 9. (c) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863- 927. (d) Faulkner, D. J. Synthesis 1971, 175-189. For recent applications of vinyl inflates: (e) Smith, A. B., III; Condon, S. M.; McCauley, J. A.; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. E., Jr. J. Am. Chem. Soc. 1997, 119, 947-961, and references cited. (f) Ritter, K. Synthesis 1993, 735-762. (g) McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1980, 21, 4313-4316. For examples of rearrangements: (h) Smith, A. B., III; Chen, S. S.-Y.; Nelson, F. C.; Reichert, J. M.; Salvatore, B. A. J. Am. Chem. Soc. 1995, 117, 12013-12014. (i) Overman, L. E.; Lin, N.- H. J. Org. Chem. 1985, 50, 3669-3670. (j) Wilson, S. R.; Price, M. F. J. Org. Chem. 1984, 49, 722-725. (k) Wakabayashi, N.; Waters, R. M.; Church, J. P. Tetrahedron Lett. 1969, 3253-3256. For the examples of phosphorus reagents: (l) Yue, X.; Li, Y. Synthesis 1996, 736-740. (m) Vedejs, E.; Cabaj, J.; Peterson, M. J. J. Org. Chem. 1993, 58, 6509- 6512. (n) Jones, T. K.; Mills, S. G.; Reamer, R. A.; Askin, D.; Desmond, R.; Volante, R. P.; Shinkai, I. J. Am. Chem. Soc. 1989, 111, 1157- 1159. (o) Schreiber, S. L.; Sammakia, T.; Uehling, D. E. J. Org. Chem. 1989, 54, 15-16. For the use of alkyne metalation strategies: (p) Wipf, P.; Smitrovich, J. H.; Moon, C.-W. J. Org. Chem. 1992, 57, 3178-3186. (q) Carr, D. B.; Schwartz, J. J. Am. Chem. Soc. 1979, 101, 3521-3531. (r) Ireland, R. E.; Wipf, P. J. Org. Chem. 1990, 55, 1425-1426. (s) Marfat, A.; McGuirk, P. R.; Helquist, P. J. Org. Chem. 1978, 44, 3888- 3901.
14. For leading references see: (a) Smith, A. B., III; Condon, S. M.; McCauley, J. A. Acc. Chem. Res. 1998, 31, 35-46. (b) Westwell, A. D.; Williams, J. M. J. In Preparation of Alkenes: A Practical Approach; Williams, J. M. J., Ed.; Oxford University Press: New York, 1996; Chapter 9. (c) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863- 927. (d) Faulkner, D. J. Synthesis 1971, 175-189. For recent applications of vinyl inflates: (e) Smith, A. B., III; Condon, S. M.; McCauley, J. A.; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. E., Jr. J. Am. Chem. Soc. 1997, 119, 947-961, and references cited. (f) Ritter, K. Synthesis 1993, 735-762. (g) McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1980, 21, 4313-4316. For examples of rearrangements: (h) Smith, A. B., III; Chen, S. S.-Y.; Nelson, F. C.; Reichert, J. M.; Salvatore, B. A. J. Am. Chem. Soc. 1995, 117, 12013-12014. (i) Overman, L. E.; Lin, N.- H. J. Org. Chem. 1985, 50, 3669-3670. (j) Wilson, S. R.; Price, M. F. J. Org. Chem. 1984, 49, 722-725. (k) Wakabayashi, N.; Waters, R. M.; Church, J. P. Tetrahedron Lett. 1969, 3253-3256. For the examples of phosphorus reagents: (l) Yue, X.; Li, Y. Synthesis 1996, 736-740. (m) Vedejs, E.; Cabaj, J.; Peterson, M. J. J. Org. Chem. 1993, 58, 6509- 6512. (n) Jones, T. K.; Mills, S. G.; Reamer, R. A.; Askin, D.; Desmond, R.; Volante, R. P.; Shinkai, I. J. Am. Chem. Soc. 1989, 111, 1157- 1159. (o) Schreiber, S. L.; Sammakia, T.; Uehling, D. E. J. Org. Chem. 1989, 54, 15-16. For the use of alkyne metalation strategies: (p) Wipf, P.; Smitrovich, J. H.; Moon, C.-W. J. Org. Chem. 1992, 57, 3178-3186. (q) Carr, D. B.; Schwartz, J. J. Am. Chem. Soc. 1979, 101, 3521-3531. (r) Ireland, R. E.; Wipf, P. J. Org. Chem. 1990, 55, 1425-1426. (s) Marfat, A.; McGuirk, P. R.; Helquist, P. J. Org. Chem. 1978, 44, 3888- 3901.
15. For leading references see: (a) Smith, A. B., III; Condon, S. M.; McCauley, J. A. Acc. Chem. Res. 1998, 31, 35-46. (b) Westwell, A. D.; Williams, J. M. J. In Preparation of Alkenes: A Practical Approach; Williams, J. M. J., Ed.; Oxford University Press: New York, 1996; Chapter 9. (c) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863- 927. (d) Faulkner, D. J. Synthesis 1971, 175-189. For recent applications of vinyl inflates: (e) Smith, A. B., III; Condon, S. M.; McCauley, J. A.; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. E., Jr. J. Am. Chem. Soc. 1997, 119, 947-961, and references cited. (f) Ritter, K. Synthesis 1993, 735-762. (g) McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1980, 21, 4313-4316. For examples of rearrangements: (h) Smith, A. B., III; Chen, S. S.-Y.; Nelson, F. C.; Reichert, J. M.; Salvatore, B. A. J. Am. Chem. Soc. 1995, 117, 12013-12014. (i) Overman, L. E.; Lin, N.- H. J. Org. Chem. 1985, 50, 3669-3670. (j) Wilson, S. R.; Price, M. F. J. Org. Chem. 1984, 49, 722-725. (k) Wakabayashi, N.; Waters, R. M.; Church, J. P. Tetrahedron Lett. 1969, 3253-3256. For the examples of phosphorus reagents: (l) Yue, X.; Li, Y. Synthesis 1996, 736-740. (m) Vedejs, E.; Cabaj, J.; Peterson, M. J. J. Org. Chem. 1993, 58, 6509- 6512. (n) Jones, T. K.; Mills, S. G.; Reamer, R. A.; Askin, D.; Desmond, R.; Volante, R. P.; Shinkai, I. J. Am. Chem. Soc. 1989, 111, 1157- 1159. (o) Schreiber, S. L.; Sammakia, T.; Uehling, D. E. J. Org. Chem. 1989, 54, 15-16. For the use of alkyne metalation strategies: (p) Wipf, P.; Smitrovich, J. H.; Moon, C.-W. J. Org. Chem. 1992, 57, 3178-3186. (q) Carr, D. B.; Schwartz, J. J. Am. Chem. Soc. 1979, 101, 3521-3531. (r) Ireland, R. E.; Wipf, P. J. Org. Chem. 1990, 55, 1425-1426. (s) Marfat, A.; McGuirk, P. R.; Helquist, P. J. Org. Chem. 1978, 44, 3888- 3901.
16. For leading references see: (a) Smith, A. B., III; Condon, S. M.; McCauley, J. A. Acc. Chem. Res. 1998, 31, 35-46. (b) Westwell, A. D.; Williams, J. M. J. In Preparation of Alkenes: A Practical Approach; Williams, J. M. J., Ed.; Oxford University Press: New York, 1996; Chapter 9. (c) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863- 927. (d) Faulkner, D. J. Synthesis 1971, 175-189. For recent applications of vinyl inflates: (e) Smith, A. B., III; Condon, S. M.; McCauley, J. A.; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. E., Jr. J. Am. Chem. Soc. 1997, 119, 947-961, and references cited. (f) Ritter, K. Synthesis 1993, 735-762. (g) McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1980, 21, 4313-4316. For examples of rearrangements: (h) Smith, A. B., III; Chen, S. S.-Y.; Nelson, F. C.; Reichert, J. M.; Salvatore, B. A. J. Am. Chem. Soc. 1995, 117, 12013-12014. (i) Overman, L. E.; Lin, N.-H. J. Org. Chem. 1985, 50, 3669-3670. (j) Wilson, S. R.; Price, M. F. J. Org. Chem. 1984, 49, 722-725. (k) Wakabayashi, N.; Waters, R. M.; Church, J. P. Tetrahedron Lett. 1969, 3253-3256. For the examples of phosphorus reagents: (l) Yue, X.; Li, Y. Synthesis 1996, 736-740. (m) Vedejs, E.; Cabaj, J.; Peterson, M. J. J. Org. Chem. 1993, 58, 6509- 6512. (n) Jones, T. K.; Mills, S. G.; Reamer, R. A.; Askin, D.; Desmond, R.; Volante, R. P.; Shinkai, I. J. Am. Chem. Soc. 1989, 111, 1157- 1159. (o) Schreiber, S. L.; Sammakia, T.; Uehling, D. E. J. Org. Chem. 1989, 54, 15-16. For the use of alkyne metalation strategies: (p) Wipf, P.; Smitrovich, J. H.; Moon, C.-W. J. Org. Chem. 1992, 57, 3178-3186. (q) Carr, D. B.; Schwartz, J. J. Am. Chem. Soc. 1979, 101, 3521-3531. (r) Ireland, R. E.; Wipf, P. J. Org. Chem. 1990, 55, 1425-1426. (s) Marfat, A.; McGuirk, P. R.; Helquist, P. J. Org. Chem. 1978, 44, 3888- 3901.
17. For leading references see: (a) Smith, A. B., III; Condon, S. M.; McCauley, J. A. Acc. Chem. Res. 1998, 31, 35-46. (b) Westwell, A. D.; Williams, J. M. J. In Preparation of Alkenes: A Practical Approach; Williams, J. M. J., Ed.; Oxford University Press: New York, 1996; Chapter 9. (c) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863- 927. (d) Faulkner, D. J. Synthesis 1971, 175-189. For recent applications of vinyl inflates: (e) Smith, A. B., III; Condon, S. M.; McCauley, J. A.; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. E., Jr. J. Am. Chem. Soc. 1997, 119, 947-961, and references cited. (f) Ritter, K. Synthesis 1993, 735-762. (g) McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1980, 21, 4313-4316. For examples of rearrangements: (h) Smith, A. B., III; Chen, S. S.-Y.; Nelson, F. C.; Reichert, J. M.; Salvatore, B. A. J. Am. Chem. Soc. 1995, 117, 12013-12014. (i) Overman, L. E.; Lin, N.- H. J. Org. Chem. 1985, 50, 3669-3670. (j) Wilson, S. R.; Price, M. F. J. Org. Chem. 1984, 49, 722-725. (k) Wakabayashi, N.; Waters, R. M.; Church, J. P. Tetrahedron Lett. 1969, 3253-3256. For the examples of phosphorus reagents: (l) Yue, X.; Li, Y. Synthesis 1996, 736-740. (m) Vedejs, E.; Cabaj, J.; Peterson, M. J. J. Org. Chem. 1993, 58, 6509- 6512. (n) Jones, T. K.; Mills, S. G.; Reamer, R. A.; Askin, D.; Desmond, R.; Volante, R. P.; Shinkai, I. J. Am. Chem. Soc. 1989, 111, 1157- 1159. (o) Schreiber, S. L.; Sammakia, T.; Uehling, D. E. J. Org. Chem. 1989, 54, 15-16. For the use of alkyne metalation strategies: (p) Wipf, P.; Smitrovich, J. H.; Moon, C.-W. J. Org. Chem. 1992, 57, 3178-3186. (q) Carr, D. B.; Schwartz, J. J. Am. Chem. Soc. 1979, 101, 3521-3531. (r) Ireland, R. E.; Wipf, P. J. Org. Chem. 1990, 55, 1425-1426. (s) Marfat, A.; McGuirk, P. R.; Helquist, P. J. Org. Chem. 1978, 44, 3888- 3901.
18. For leading references see: (a) Smith, A. B., III; Condon, S. M.; McCauley, J. A. Acc. Chem. Res. 1998, 31, 35-46. (b) Westwell, A. D.; Williams, J. M. J. In Preparation of Alkenes: A Practical Approach; Williams, J. M. J., Ed.; Oxford University Press: New York, 1996; Chapter 9. (c) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863- 927. (d) Faulkner, D. J. Synthesis 1971, 175-189. For recent applications of vinyl inflates: (e) Smith, A. B., III; Condon, S. M.; McCauley, J. A.; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. E., Jr. J. Am. Chem. Soc. 1997, 119, 947-961, and references cited. (f) Ritter, K. Synthesis 1993, 735-762. (g) McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1980, 21, 4313-4316. For examples of rearrangements: (h) Smith, A. B., III; Chen, S. S.-Y.; Nelson, F. C.; Reichert, J. M.; Salvatore, B. A. J. Am. Chem. Soc. 1995, 117, 12013-12014. (i) Overman, L. E.; Lin, N.- H. J. Org. Chem. 1985, 50, 3669-3670. (j) Wilson, S. R.; Price, M. F. J. Org. Chem. 1984, 49, 722-725. (k) Wakabayashi, N.; Waters, R. M.; Church, J. P. Tetrahedron Lett. 1969, 3253-3256. For the examples of phosphorus reagents: (l) Yue, X.; Li, Y. Synthesis 1996, 736-740. (m) Vedejs, E.; Cabaj, J.; Peterson, M. J. J. Org. Chem. 1993, 58, 6509- 6512. (n) Jones, T. K.; Mills, S. G.; Reamer, R. A.; Askin, D.; Desmond, R.; Volante, R. P.; Shinkai, I. J. Am. Chem. Soc. 1989, 111, 1157- 1159. (o) Schreiber, S. L.; Sammakia, T.; Uehling, D. E. J. Org. Chem. 1989, 54, 15-16. For the use of alkyne metalation strategies: (p) Wipf, P.; Smitrovich, J. H.; Moon, C.-W. J. Org. Chem. 1992, 57, 3178-3186. (q) Carr, D. B.; Schwartz, J. J. Am. Chem. Soc. 1979, 101, 3521-3531. (r) Ireland, R. E.; Wipf, P. J. Org. Chem. 1990, 55, 1425-1426. (s) Marfat, A.; McGuirk, P. R.; Helquist, P. J. Org. Chem. 1978, 44, 3888- 3901.
19. For leading references see: (a) Smith, A. B., III; Condon, S. M.; McCauley, J. A. Acc. Chem. Res. 1998, 31, 35-46. (b) Westwell, A. D.; Williams, J. M. J. In Preparation of Alkenes: A Practical Approach; Williams, J. M. J., Ed.; Oxford University Press: New York, 1996; Chapter 9. (c) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863- 927. (d) Faulkner, D. J. Synthesis 1971, 175-189. For recent applications of vinyl inflates: (e) Smith, A. B., III; Condon, S. M.; McCauley, J. A.; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. E., Jr. J. Am. Chem. Soc. 1997, 119, 947-961, and references cited. (f) Ritter, K. Synthesis 1993, 735-762. (g) McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1980, 21, 4313-4316. For examples of rearrangements: (h) Smith, A. B., III; Chen, S. S.-Y.; Nelson, F. C.; Reichert, J. M.; Salvatore, B. A. J. Am. Chem. Soc. 1995, 117, 12013-12014. (i) Overman, L. E.; Lin, N.- H. J. Org. Chem. 1985, 50, 3669-3670. (j) Wilson, S. R.; Price, M. F. J. Org. Chem. 1984, 49, 722-725. (k) Wakabayashi, N.; Waters, R. M.; Church, J. P. Tetrahedron Lett. 1969, 3253-3256. For the examples of phosphorus reagents: (l) Yue, X.; Li, Y. Synthesis 1996, 736-740. (m) Vedejs, E.; Cabaj, J.; Peterson, M. J. J. Org. Chem. 1993, 58, 6509- 6512. (n) Jones, T. K.; Mills, S. G.; Reamer, R. A.; Askin, D.; Desmond, R.; Volante, R. P.; Shinkai, I. J. Am. Chem. Soc. 1989, 111, 1157- 1159. (o) Schreiber, S. L.; Sammakia, T.; Uehling, D. E. J. Org. Chem. 1989, 54, 15-16. For the use of alkyne metalation strategies: (p) Wipf, P.; Smitrovich, J. H.; Moon, C.-W. J. Org. Chem. 1992, 57, 3178-3186. (q) Carr, D. B.; Schwartz, J. J. Am. Chem. Soc. 1979, 101, 3521-3531. (r) Ireland, R. E.; Wipf, P. J. Org. Chem. 1990, 55, 1425-1426. (s) Marfat, A.; McGuirk, P. R.; Helquist, P. J. Org. Chem. 1978, 44, 3888- 3901.
20. For leading references see: (a) Smith, A. B., III; Condon, S. M.; McCauley, J. A. Acc. Chem. Res. 1998, 31, 35-46. (b) Westwell, A. D.; Williams, J. M. J. In Preparation of Alkenes: A Practical Approach; Williams, J. M. J., Ed.; Oxford University Press: New York, 1996; Chapter 9. (c) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863- 927. (d) Faulkner, D. J. Synthesis 1971, 175-189. For recent applications of vinyl inflates: (e) Smith, A. B., III; Condon, S. M.; McCauley, J. A.; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. E., Jr. J. Am. Chem. Soc. 1997, 119, 947-961, and references cited. (f) Ritter, K. Synthesis 1993, 735-762. (g) McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1980, 21, 4313-4316. For examples of rearrangements: (h) Smith, A. B., III; Chen, S. S.-Y.; Nelson, F. C.; Reichert, J. M.; Salvatore, B. A. J. Am. Chem. Soc. 1995, 117, 12013-12014. (i) Overman, L. E.; Lin, N.- H. J. Org. Chem. 1985, 50, 3669-3670. (j) Wilson, S. R.; Price, M. F. J. Org. Chem. 1984, 49, 722-725. (k) Wakabayashi, N.; Waters, R. M.; Church, J. P. Tetrahedron Lett. 1969, 3253-3256. For the examples of phosphorus reagents: (l) Yue, X.; Li, Y. Synthesis 1996, 736-740. (m) Vedejs, E.; Cabaj, J.; Peterson, M. J. J. Org. Chem. 1993, 58, 6509-6512. (n) Jones, T. K.; Mills, S. G.; Reamer, R. A.; Askin, D.; Desmond, R.; Volante, R. P.; Shinkai, I. J. Am. Chem. Soc. 1989, 111, 1157- 1159. (o) Schreiber, S. L.; Sammakia, T.; Uehling, D. E. J. Org. Chem. 1989, 54, 15-16. For the use of alkyne metalation strategies: (p) Wipf, P.; Smitrovich, J. H.; Moon, C.-W. J. Org. Chem. 1992, 57, 3178-3186. (q) Carr, D. B.; Schwartz, J. J. Am. Chem. Soc. 1979, 101, 3521-3531. (r) Ireland, R. E.; Wipf, P. J. Org. Chem. 1990, 55, 1425-1426. (s) Marfat, A.; McGuirk, P. R.; Helquist, P. J. Org. Chem. 1978, 44, 3888- 3901.
21. For leading references see: (a) Smith, A. B., III; Condon, S. M.; McCauley, J. A. Acc. Chem. Res. 1998, 31, 35-46. (b) Westwell, A. D.; Williams, J. M. J. In Preparation of Alkenes: A Practical Approach; Williams, J. M. J., Ed.; Oxford University Press: New York, 1996; Chapter 9. (c) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863- 927. (d) Faulkner, D. J. Synthesis 1971, 175-189. For recent applications of vinyl inflates: (e) Smith, A. B., III; Condon, S. M.; McCauley, J. A.; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. E., Jr. J. Am. Chem. Soc. 1997, 119, 947-961, and references cited. (f) Ritter, K. Synthesis 1993, 735-762. (g) McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1980, 21, 4313-4316. For examples of rearrangements: (h) Smith, A. B., III; Chen, S. S.-Y.; Nelson, F. C.; Reichert, J. M.; Salvatore, B. A. J. Am. Chem. Soc. 1995, 117, 12013-12014. (i) Overman, L. E.; Lin, N.- H. J. Org. Chem. 1985, 50, 3669-3670. (j) Wilson, S. R.; Price, M. F. J. Org. Chem. 1984, 49, 722-725. (k) Wakabayashi, N.; Waters, R. M.; Church, J. P. Tetrahedron Lett. 1969, 3253-3256. For the examples of phosphorus reagents: (l) Yue, X.; Li, Y. Synthesis 1996, 736-740. (m) Vedejs, E.; Cabaj, J.; Peterson, M. J. J. Org. Chem. 1993, 58, 6509- 6512. (n) Jones, T. K.; Mills, S. G.; Reamer, R. A.; Askin, D.; Desmond, R.; Volante, R. P.; Shinkai, I. J. Am. Chem. Soc. 1989, 111, 1157-1159. (o) Schreiber, S. L.; Sammakia, T.; Uehling, D. E. J. Org. Chem. 1989, 54, 15-16. For the use of alkyne metalation strategies: (p) Wipf, P.; Smitrovich, J. H.; Moon, C.-W. J. Org. Chem. 1992, 57, 3178-3186. (q) Carr, D. B.; Schwartz, J. J. Am. Chem. Soc. 1979, 101, 3521-3531. (r) Ireland, R. E.; Wipf, P. J. Org. Chem. 1990, 55, 1425-1426. (s) Marfat, A.; McGuirk, P. R.; Helquist, P. J. Org. Chem. 1978, 44, 3888- 3901.
22. For leading references see: (a) Smith, A. B., III; Condon, S. M.; McCauley, J. A. Acc. Chem. Res. 1998, 31, 35-46. (b) Westwell, A. D.; Williams, J. M. J. In Preparation of Alkenes: A Practical Approach; Williams, J. M. J., Ed.; Oxford University Press: New York, 1996; Chapter 9. (c) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863- 927. (d) Faulkner, D. J. Synthesis 1971, 175-189. For recent applications of vinyl inflates: (e) Smith, A. B., III; Condon, S. M.; McCauley, J. A.; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. E., Jr. J. Am. Chem. Soc. 1997, 119, 947-961, and references cited. (f) Ritter, K. Synthesis 1993, 735-762. (g) McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1980, 21, 4313-4316. For examples of rearrangements: (h) Smith, A. B., III; Chen, S. S.-Y.; Nelson, F. C.; Reichert, J. M.; Salvatore, B. A. J. Am. Chem. Soc. 1995, 117, 12013-12014. (i) Overman, L. E.; Lin, N.- H. J. Org. Chem. 1985, 50, 3669-3670. (j) Wilson, S. R.; Price, M. F. J. Org. Chem. 1984, 49, 722-725. (k) Wakabayashi, N.; Waters, R. M.; Church, J. P. Tetrahedron Lett. 1969, 3253-3256. For the examples of phosphorus reagents: (l) Yue, X.; Li, Y. Synthesis 1996, 736-740. (m) Vedejs, E.; Cabaj, J.; Peterson, M. J. J. Org. Chem. 1993, 58, 6509- 6512. (n) Jones, T. K.; Mills, S. G.; Reamer, R. A.; Askin, D.; Desmond, R.; Volante, R. P.; Shinkai, I. J. Am. Chem. Soc. 1989, 111, 1157- 1159. (o) Schreiber, S. L.; Sammakia, T.; Uehling, D. E. J. Org. Chem. 1989, 54, 15-16. For the use of alkyne metalation strategies: (p) Wipf, P.; Smitrovich, J. H.; Moon, C.-W. J. Org. Chem. 1992, 57, 3178-3186. (q) Carr, D. B.; Schwartz, J. J. Am. Chem. Soc. 1979, 101, 3521-3531. (r) Ireland, R. E.; Wipf, P. J. Org. Chem. 1990, 55, 1425-1426. (s) Marfat, A.; McGuirk, P. R.; Helquist, P. J. Org. Chem. 1978, 44, 3888- 3901.
23. For leading references see: (a) Smith, A. B., III; Condon, S. M.; McCauley, J. A. Acc. Chem. Res. 1998, 31, 35-46. (b) Westwell, A. D.; Williams, J. M. J. In Preparation of Alkenes: A Practical Approach; Williams, J. M. J., Ed.; Oxford University Press: New York, 1996; Chapter 9. (c) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863- 927. (d) Faulkner, D. J. Synthesis 1971, 175-189. For recent applications of vinyl inflates: (e) Smith, A. B., III; Condon, S. M.; McCauley, J. A.; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. E., Jr. J. Am. Chem. Soc. 1997, 119, 947-961, and references cited. (f) Ritter, K. Synthesis 1993, 735-762. (g) McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1980, 21, 4313-4316. For examples of rearrangements: (h) Smith, A. B., III; Chen, S. S.-Y.; Nelson, F. C.; Reichert, J. M.; Salvatore, B. A. J. Am. Chem. Soc. 1995, 117, 12013-12014. (i) Overman, L. E.; Lin, N.- H. J. Org. Chem. 1985, 50, 3669-3670. (j) Wilson, S. R.; Price, M. F. J. Org. Chem. 1984, 49, 722-725. (k) Wakabayashi, N.; Waters, R. M.; Church, J. P. Tetrahedron Lett. 1969, 3253-3256. For the examples of phosphorus reagents: (l) Yue, X.; Li, Y. Synthesis 1996, 736-740. (m) Vedejs, E.; Cabaj, J.; Peterson, M. J. J. Org. Chem. 1993, 58, 6509- 6512. (n) Jones, T. K.; Mills, S. G.; Reamer, R. A.; Askin, D.; Desmond, R.; Volante, R. P.; Shinkai, I. J. Am. Chem. Soc. 1989, 111, 1157- 1159. (o) Schreiber, S. L.; Sammakia, T.; Uehling, D. E. J. Org. Chem. 1989, 54, 15-16. For the use of alkyne metalation strategies: (p) Wipf, P.; Smitrovich, J. H.; Moon, C.-W. J. Org. Chem. 1992, 57, 3178-3186. (q) Carr, D. B.; Schwartz, J. J. Am. Chem. Soc. 1979, 101, 3521-3531. (r) Ireland, R. E.; Wipf, P. J. Org. Chem. 1990, 55, 1425-1426. (s) Marfat, A.; McGuirk, P. R.; Helquist, P. J. Org. Chem. 1978, 44, 3888- 3901.
24. For leading references see: (a) Smith, A. B., III; Condon, S. M.; McCauley, J. A. Acc. Chem. Res. 1998, 31, 35-46. (b) Westwell, A. D.; Williams, J. M. J. In Preparation of Alkenes: A Practical Approach; Williams, J. M. J., Ed.; Oxford University Press: New York, 1996; Chapter 9. (c) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863- 927. (d) Faulkner, D. J. Synthesis 1971, 175-189. For recent applications of vinyl inflates: (e) Smith, A. B., III; Condon, S. M.; McCauley, J. A.; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. E., Jr. J. Am. Chem. Soc. 1997, 119, 947-961, and references cited. (f) Ritter, K. Synthesis 1993, 735-762. (g) McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1980, 21, 4313-4316. For examples of rearrangements: (h) Smith, A. B., III; Chen, S. S.-Y.; Nelson, F. C.; Reichert, J. M.; Salvatore, B. A. J. Am. Chem. Soc. 1995, 117, 12013-12014. (i) Overman, L. E.; Lin, N.- H. J. Org. Chem. 1985, 50, 3669-3670. (j) Wilson, S. R.; Price, M. F. J. Org. Chem. 1984, 49, 722-725. (k) Wakabayashi, N.; Waters, R. M.; Church, J. P. Tetrahedron Lett. 1969, 3253-3256. For the examples of phosphorus reagents: (l) Yue, X.; Li, Y. Synthesis 1996, 736-740. (m) Vedejs, E.; Cabaj, J.; Peterson, M. J. J. Org. Chem. 1993, 58, 6509- 6512. (n) Jones, T. K.; Mills, S. G.; Reamer, R. A.; Askin, D.; Desmond, R.; Volante, R. P.; Shinkai, I. J. Am. Chem. Soc. 1989, 111, 1157- 1159. (o) Schreiber, S. L.; Sammakia, T.; Uehling, D. E. J. Org. Chem. 1989, 54, 15-16. For the use of alkyne metalation strategies: (p) Wipf, P.; Smitrovich, J. H.; Moon, C.-W. J. Org. Chem. 1992, 57, 3178-3186. (q) Carr, D. B.; Schwartz, J. J. Am. Chem. Soc. 1979, 101, 3521-3531. (r) Ireland, R. E.; Wipf, P. J. Org. Chem. 1990, 55, 1425-1426. (s) Marfat, A.; McGuirk, P. R.; Helquist, P. J. Org. Chem. 1978, 44, 3888- 3901.
25. For leading references see: (a) Smith, A. B., III; Condon, S. M.; McCauley, J. A. Acc. Chem. Res. 1998, 31, 35-46. (b) Westwell, A. D.; Williams, J. M. J. In Preparation of Alkenes: A Practical Approach; Williams, J. M. J., Ed.; Oxford University Press: New York, 1996; Chapter 9. (c) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863- 927. (d) Faulkner, D. J. Synthesis 1971, 175-189. For recent applications of vinyl inflates: (e) Smith, A. B., III; Condon, S. M.; McCauley, J. A.; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. E., Jr. J. Am. Chem. Soc. 1997, 119, 947-961, and references cited. (f) Ritter, K. Synthesis 1993, 735-762. (g) McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1980, 21, 4313-4316. For examples of rearrangements: (h) Smith, A. B., III; Chen, S. S.-Y.; Nelson, F. C.; Reichert, J. M.; Salvatore, B. A. J. Am. Chem. Soc. 1995, 117, 12013-12014. (i) Overman, L. E.; Lin, N.- H. J. Org. Chem. 1985, 50, 3669-3670. (j) Wilson, S. R.; Price, M. F. J. Org. Chem. 1984, 49, 722-725. (k) Wakabayashi, N.; Waters, R. M.; Church, J. P. Tetrahedron Lett. 1969, 3253-3256. For the examples of phosphorus reagents: (l) Yue, X.; Li, Y. Synthesis 1996, 736-740. (m) Vedejs, E.; Cabaj, J.; Peterson, M. J. J. Org. Chem. 1993, 58, 6509- 6512. (n) Jones, T. K.; Mills, S. G.; Reamer, R. A.; Askin, D.; Desmond, R.; Volante, R. P.; Shinkai, I. J. Am. Chem. Soc. 1989, 111, 1157- 1159. (o) Schreiber, S. L.; Sammakia, T.; Uehling, D. E. J. Org. Chem. 1989, 54, 15-16. For the use of alkyne metalation strategies: (p) Wipf, P.; Smitrovich, J. H.; Moon, C.-W. J. Org. Chem. 1992, 57, 3178-3186. (q) Carr, D. B.; Schwartz, J. J. Am. Chem. Soc. 1979, 101, 3521-3531. (r) Ireland, R. E.; Wipf, P. J. Org. Chem. 1990, 55, 1425-1426. (s) Marfat, A.; McGuirk, P. R.; Helquist, P. J. Org. Chem. 1978, 44, 3888- 3901.
26. For leading references see: (a) Smith, A. B., III; Condon, S. M.; McCauley, J. A. Acc. Chem. Res. 1998, 31, 35-46. (b) Westwell, A. D.; Williams, J. M. J. In Preparation of Alkenes: A Practical Approach; Williams, J. M. J., Ed.; Oxford University Press: New York, 1996; Chapter 9. (c) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863- 927. (d) Faulkner, D. J. Synthesis 1971, 175-189. For recent applications of vinyl inflates: (e) Smith, A. B., III; Condon, S. M.; McCauley, J. A.; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. E., Jr. J. Am. Chem. Soc. 1997, 119, 947-961, and references cited. (f) Ritter, K. Synthesis 1993, 735-762. (g) McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1980, 21, 4313-4316. For examples of rearrangements: (h) Smith, A. B., III; Chen, S. S.-Y.; Nelson, F. C.; Reichert, J. M.; Salvatore, B. A. J. Am. Chem. Soc. 1995, 117, 12013-12014. (i) Overman, L. E.; Lin, N.- H. J. Org. Chem. 1985, 50, 3669-3670. (j) Wilson, S. R.; Price, M. F. J. Org. Chem. 1984, 49, 722-725. (k) Wakabayashi, N.; Waters, R. M.; Church, J. P. Tetrahedron Lett. 1969, 3253-3256. For the examples of phosphorus reagents: (l) Yue, X.; Li, Y. Synthesis 1996, 736-740. (m) Vedejs, E.; Cabaj, J.; Peterson, M. J. J. Org. Chem. 1993, 58, 6509- 6512. (n) Jones, T. K.; Mills, S. G.; Reamer, R. A.; Askin, D.; Desmond, R.; Volante, R. P.; Shinkai, I. J. Am. Chem. Soc. 1989, 111, 1157- 1159. (o) Schreiber, S. L.; Sammakia, T.; Uehling, D. E. J. Org. Chem. 1989, 54, 15-16. For the use of alkyne metalation strategies: (p) Wipf, P.; Smitrovich, J. H.; Moon, C.-W. J. Org. Chem. 1992, 57, 3178-3186. (q) Carr, D. B.; Schwartz, J. J. Am. Chem. Soc. 1979, 101, 3521-3531. (r) Ireland, R. E.; Wipf, P. J. Org. Chem. 1990, 55, 1425-1426. (s) Marfat, A.; McGuirk, P. R.; Helquist, P. J. Org. Chem. 1978, 44, 3888-3901.
27. (a) Ito, H.; Imai, N.; Tanikawa, S.; Kobayashi, S. Tetrahedron Lett. 1996, 37, 1795-1798.
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35. Hanessian, S.; Lavallée, P. Can. J. Chem. 1976, 53, 2975-2977.
36. (a) Tse, B. J. Am. Chem. Soc. 1996, 118, 7094-7100.
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40. 2: (e) Künzer, H.; Stahnke, M.; Sauer, G.; Wiechert, R. Tetrahedron Lett. 1991, 32, 1949-1952.
41. 2: (e) Künzer, H.; Stahnke, M.; Sauer, G.; Wiechert, R. Tetrahedron Lett. 1991, 32, 1949-1952.
42. 2: (e) Künzer, H.; Stahnke, M.; Sauer, G.; Wiechert, R. Tetrahedron Lett. 1991, 32, 1949-1952.
43. 2: (e) Künzer, H.; Stahnke, M.; Sauer, G.; Wiechert, R. Tetrahedron Lett. 1991, 32, 1949-1952.
44. (a) Kende, A. S.; Liu, K.; Kaldor, I.; Dorey, G.; Koch, K. J. Am. Chem. Soc. 1995, 117, 8258-8270.
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46. (c) Mohri, M.; Kinoshita, H.; Inomata, K.; Kotake, H. Chem. Lett. 1985, 451-454.
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49. For similar problems in reducing homoallylic alcohols see: Brown, M. J.; Harrison, T.; Overman, L. E. J. Am. Chem. Soc. 1991, 113, 5378-5384.
50. For leading references on the difficulty of the selective reduction of conjugated dienes: (a) James, B. R. Compr. Organomet. Chem. Wilkinson, G., Stone, F. G. A., Abell, E. W., Eds.; 1982, Vol 8.; Chapter 51, pp 285-369. For reductions with diimide: (b) Pasto, D. J.; Taylor, R. T. Org. React. 1991, 40, 91-155. (c) Siegel, S.; Foreman, M.; Fisher, R. P.; Johnson, S. E. J. Org. Chem. 1975, 40, 3599-3601. For homogeneous catalysts: (d) Reger, D. L.; Habib, M. M.; Fauth, D. J. J. Org. Chem. 1980, 45, 3860-3865. (e) Kawakami, K; Mizoroki, T.; Ozaki, A. Chem. Lett. 1976, 847-848. (f) Birch, A. J.; Williamson, D. N. Org. React. 1976, 24, 1-186. For heterogeneous catalysts: (g) Card, R. J.; Neckers, D. C. Isr. J. Chem. 1978, 17, 269-273. (h) Cortese, N. A.; Heck, R. F. J. Org. Chem. 1978, 43 (3), 3985-3986. For some successful selective reductions: (i) Wender, P. A.; Holt, D. A. J. Am. Chem. Soc. 1985, 107, 7771-7772. (j) Choudary, B. M.; Sharma, G. V. M.; Bharathi, P. Angew. Chem., Int. Ed. Engl. 1989, 28, 465-466.
51. For leading references on the difficulty of the selective reduction of conjugated dienes: (a) James, B. R. Compr. Organomet. Chem. Wilkinson, G., Stone, F. G. A., Abell, E. W., Eds.; 1982, Vol 8.; Chapter 51, pp 285-369. For reductions with diimide: (b) Pasto, D. J.; Taylor, R. T. Org. React. 1991, 40, 91-155. (c) Siegel, S.; Foreman, M.; Fisher, R. P.; Johnson, S. E. J. Org. Chem. 1975, 40, 3599-3601. For homogeneous catalysts: (d) Reger, D. L.; Habib, M. M.; Fauth, D. J. J. Org. Chem. 1980, 45, 3860-3865. (e) Kawakami, K; Mizoroki, T.; Ozaki, A. Chem. Lett. 1976, 847-848. (f) Birch, A. J.; Williamson, D. N. Org. React. 1976, 24, 1-186. For heterogeneous catalysts: (g) Card, R. J.; Neckers, D. C. Isr. J. Chem. 1978, 17, 269-273. (h) Cortese, N. A.; Heck, R. F. J. Org. Chem. 1978, 43 (3), 3985-3986. For some successful selective reductions: (i) Wender, P. A.; Holt, D. A. J. Am. Chem. Soc. 1985, 107, 7771-7772. (j) Choudary, B. M.; Sharma, G. V. M.; Bharathi, P. Angew. Chem., Int. Ed. Engl. 1989, 28, 465-466.
52. For leading references on the difficulty of the selective reduction of conjugated dienes: (a) James, B. R. Compr. Organomet. Chem. Wilkinson, G., Stone, F. G. A., Abell, E. W., Eds.; 1982, Vol 8.; Chapter 51, pp 285-369. For reductions with diimide: (b) Pasto, D. J.; Taylor, R. T. Org. React. 1991, 40, 91-155. (c) Siegel, S.; Foreman, M.; Fisher, R. P.; Johnson, S. E. J. Org. Chem. 1975, 40, 3599-3601. For homogeneous catalysts: (d) Reger, D. L.; Habib, M. M.; Fauth, D. J. J. Org. Chem. 1980, 45, 3860-3865. (e) Kawakami, K; Mizoroki, T.; Ozaki, A. Chem. Lett. 1976, 847-848. (f) Birch, A. J.; Williamson, D. N. Org. React. 1976, 24, 1-186. For heterogeneous catalysts: (g) Card, R. J.; Neckers, D. C. Isr. J. Chem. 1978, 17, 269-273. (h) Cortese, N. A.; Heck, R. F. J. Org. Chem. 1978, 43 (3), 3985-3986. For some successful selective reductions: (i) Wender, P. A.; Holt, D. A. J. Am. Chem. Soc. 1985, 107, 7771-7772. (j) Choudary, B. M.; Sharma, G. V. M.; Bharathi, P. Angew. Chem., Int. Ed. Engl. 1989, 28, 465-466.
53. For leading references on the difficulty of the selective reduction of conjugated dienes: (a) James, B. R. Compr. Organomet. Chem. Wilkinson, G., Stone, F. G. A., Abell, E. W., Eds.; 1982, Vol 8.; Chapter 51, pp 285-369. For reductions with diimide: (b) Pasto, D. J.; Taylor, R. T. Org. React. 1991, 40, 91-155. (c) Siegel, S.; Foreman, M.; Fisher, R. P.; Johnson, S. E. J. Org. Chem. 1975, 40, 3599-3601. For homogeneous catalysts: (d) Reger, D. L.; Habib, M. M.; Fauth, D. J. J. Org. Chem. 1980, 45, 3860-3865. (e) Kawakami, K; Mizoroki, T.; Ozaki, A. Chem. Lett. 1976, 847-848. (f) Birch, A. J.; Williamson, D. N. Org. React. 1976, 24, 1-186. For heterogeneous catalysts: (g) Card, R. J.; Neckers, D. C. Isr. J. Chem. 1978, 17, 269-273. (h) Cortese, N. A.; Heck, R. F. J. Org. Chem. 1978, 43 (3), 3985-3986. For some successful selective reductions: (i) Wender, P. A.; Holt, D. A. J. Am. Chem. Soc. 1985, 107, 7771-7772. (j) Choudary, B. M.; Sharma, G. V. M.; Bharathi, P. Angew. Chem., Int. Ed. Engl. 1989, 28, 465-466.
54. For leading references on the difficulty of the selective reduction of conjugated dienes: (a) James, B. R. Compr. Organomet. Chem. Wilkinson, G., Stone, F. G. A., Abell, E. W., Eds.; 1982, Vol 8.; Chapter 51, pp 285-369. For reductions with diimide: (b) Pasto, D. J.; Taylor, R. T. Org. React. 1991, 40, 91-155. (c) Siegel, S.; Foreman, M.; Fisher, R. P.; Johnson, S. E. J. Org. Chem. 1975, 40, 3599-3601. For homogeneous catalysts: (d) Reger, D. L.; Habib, M. M.; Fauth, D. J. J. Org. Chem. 1980, 45, 3860-3865. (e) Kawakami, K; Mizoroki, T.; Ozaki, A. Chem. Lett. 1976, 847-848. (f) Birch, A. J.; Williamson, D. N. Org. React. 1976, 24, 1-186. For heterogeneous catalysts: (g) Card, R. J.; Neckers, D. C. Isr. J. Chem. 1978, 17, 269-273. (h) Cortese, N. A.; Heck, R. F. J. Org. Chem. 1978, 43 (3), 3985-3986. For some successful selective reductions: (i) Wender, P. A.; Holt, D. A. J. Am. Chem. Soc. 1985, 107, 7771-7772. (j) Choudary, B. M.; Sharma, G. V. M.; Bharathi, P. Angew. Chem., Int. Ed. Engl. 1989, 28, 465-466.
55. For leading references on the difficulty of the selective reduction of conjugated dienes: (a) James, B. R. Compr. Organomet. Chem. Wilkinson, G., Stone, F. G. A., Abell, E. W., Eds.; 1982, Vol 8.; Chapter 51, pp 285-369. For reductions with diimide: (b) Pasto, D. J.; Taylor, R. T. Org. React. 1991, 40, 91-155. (c) Siegel, S.; Foreman, M.; Fisher, R. P.; Johnson, S. E. J. Org. Chem. 1975, 40, 3599-3601. For homogeneous catalysts: (d) Reger, D. L.; Habib, M. M.; Fauth, D. J. J. Org. Chem. 1980, 45, 3860-3865. (e) Kawakami, K; Mizoroki, T.; Ozaki, A. Chem. Lett. 1976, 847-848. (f) Birch, A. J.; Williamson, D. N. Org. React. 1976, 24, 1-186. For heterogeneous catalysts: (g) Card, R. J.; Neckers, D. C. Isr. J. Chem. 1978, 17, 269-273. (h) Cortese, N. A.; Heck, R. F. J. Org. Chem. 1978, 43 (3), 3985-3986. For some successful selective reductions: (i) Wender, P. A.; Holt, D. A. J. Am. Chem. Soc. 1985, 107, 7771-7772. (j) Choudary, B. M.; Sharma, G. V. M.; Bharathi, P. Angew. Chem., Int. Ed. Engl. 1989, 28, 465-466.
56. For leading references on the difficulty of the selective reduction of conjugated dienes: (a) James, B. R. Compr. Organomet. Chem. Wilkinson, G., Stone, F. G. A., Abell, E. W., Eds.; 1982, Vol 8.; Chapter 51, pp 285-369. For reductions with diimide: (b) Pasto, D. J.; Taylor, R. T. Org. React. 1991, 40, 91-155. (c) Siegel, S.; Foreman, M.; Fisher, R. P.; Johnson, S. E. J. Org. Chem. 1975, 40, 3599-3601. For homogeneous catalysts: (d) Reger, D. L.; Habib, M. M.; Fauth, D. J. J. Org. Chem. 1980, 45, 3860-3865. (e) Kawakami, K; Mizoroki, T.; Ozaki, A. Chem. Lett. 1976, 847-848. (f) Birch, A. J.; Williamson, D. N. Org. React. 1976, 24, 1-186. For heterogeneous catalysts: (g) Card, R. J.; Neckers, D. C. Isr. J. Chem. 1978, 17, 269-273. (h) Cortese, N. A.; Heck, R. F. J. Org. Chem. 1978, 43 (3), 3985-3986. For some successful selective reductions: (i) Wender, P. A.; Holt, D. A. J. Am. Chem. Soc. 1985, 107, 7771-7772. (j) Choudary, B. M.; Sharma, G. V. M.; Bharathi, P. Angew. Chem., Int. Ed. Engl. 1989, 28, 465-466.
57. For leading references on the difficulty of the selective reduction of conjugated dienes: (a) James, B. R. Compr. Organomet. Chem. Wilkinson, G., Stone, F. G. A., Abell, E. W., Eds.; 1982, Vol 8.; Chapter 51, pp 285-369. For reductions with diimide: (b) Pasto, D. J.; Taylor, R. T. Org. React. 1991, 40, 91-155. (c) Siegel, S.; Foreman, M.; Fisher, R. P.; Johnson, S. E. J. Org. Chem. 1975, 40, 3599-3601. For homogeneous catalysts: (d) Reger, D. L.; Habib, M. M.; Fauth, D. J. J. Org. Chem. 1980, 45, 3860-3865. (e) Kawakami, K; Mizoroki, T.; Ozaki, A. Chem. Lett. 1976, 847-848. (f) Birch, A. J.; Williamson, D. N. Org. React. 1976, 24, 1-186. For heterogeneous catalysts: (g) Card, R. J.; Neckers, D. C. Isr. J. Chem. 1978, 17, 269-273. (h) Cortese, N. A.; Heck, R. F. J. Org. Chem. 1978, 43 (3), 3985-3986. For some successful selective reductions: (i) Wender, P. A.; Holt, D. A. J. Am. Chem. Soc. 1985, 107, 7771-7772. (j) Choudary, B. M.; Sharma, G. V. M.; Bharathi, P. Angew. Chem., Int. Ed. Engl. 1989, 28, 465-466.
58. For leading references on the difficulty of the selective reduction of conjugated dienes: (a) James, B. R. Compr. Organomet. Chem. Wilkinson, G., Stone, F. G. A., Abell, E. W., Eds.; 1982, Vol 8.; Chapter 51, pp 285-369. For reductions with diimide: (b) Pasto, D. J.; Taylor, R. T. Org. React. 1991, 40, 91-155. (c) Siegel, S.; Foreman, M.; Fisher, R. P.; Johnson, S. E. J. Org. Chem. 1975, 40, 3599-3601. For homogeneous catalysts: (d) Reger, D. L.; Habib, M. M.; Fauth, D. J. J. Org. Chem. 1980, 45, 3860-3865. (e) Kawakami, K; Mizoroki, T.; Ozaki, A. Chem. Lett. 1976, 847-848. (f) Birch, A. J.; Williamson, D. N. Org. React. 1976, 24, 1-186. For heterogeneous catalysts: (g) Card, R. J.; Neckers, D. C. Isr. J. Chem. 1978, 17, 269-273. (h) Cortese, N. A.; Heck, R. F. J. Org. Chem. 1978, 43 (3), 3985-3986. For some successful selective reductions: (i) Wender, P. A.; Holt, D. A. J. Am. Chem. Soc. 1985, 107, 7771-7772. (j) Choudary, B. M.; Sharma, G. V. M.; Bharathi, P. Angew. Chem., Int. Ed. Engl. 1989, 28, 465-466.
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