Asymmetric total synthesis of (+)-aphanamol I based on the transition metal catalyzed [5 + 2] cycloaddition of allenes and vinylcyclopropanes

Organic Letters

Volumn 2, Issue 15, 2000, Pages 2323-2325

  Wender, Paul A ^a   Zhang, Lei ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALLENE; APHANAMOL I; AZULENE; AZULENE DERIVATIVE; CYCLOHEPTANE DERIVATIVE; CYCLOHEXENE DERIVATIVE; CYCLOPROPANE; CYCLOPROPANE DERIVATIVE; LIMONENE; POLYCYCLIC HYDROCARBON; SESQUITERPENE; TERPENE;

ARTICLE; CHEMISTRY; FRUIT; METABOLISM; STEREOISOMERISM; SYNTHESIS;

ALKADIENES; AZULENES; CYCLOHEPTANES; CYCLOHEXENES; CYCLOPROPANES; FRUIT; POLYCYCLIC COMPOUNDS; SESQUITERPENES; STEREOISOMERISM; TERPENES;

EID: 0034720925     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006085q     Document Type: Article

References (43)

1. For [4 + 4] cycloadditions, see: Wender, P. A.; IhIe, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4679. Wender P. A.; Ihle, N. C.; Correia, C. R. D. J. Am. Chem. Soc. 1988, 110, 5904-5906. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. For more recent studies, see: Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suarez-Sobrino A, Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Murakami, M.; Itami, K.; Ito, Y. Synlett 1999, S1, 951-953. For [4 + 2] cycloadditions, see: Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255-1275. For more recent studies, see: Jolly, R. S.; Luedtke. G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145-6154. O'Mahony, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443-445. Gilbertson, S. R.; Hoge, G. S. Tetrahedron Lett. 1998, 39, 2075-2078. Gilbertson, S. R.; Hoge, G. S.; Genov, D. G.; J. Org. Chem. 1998, 63, 10077-10080.
2. For [4 + 4] cycloadditions, see: Wender, P. A.; IhIe, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4679. Wender P. A.; Ihle, N. C.; Correia, C. R. D. J. Am. Chem. Soc. 1988, 110, 5904-5906. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. For more recent studies, see: Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suarez-Sobrino A, Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Murakami, M.; Itami, K.; Ito, Y. Synlett 1999, S1, 951-953. For [4 + 2] cycloadditions, see: Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255-1275. For more recent studies, see: Jolly, R. S.; Luedtke. G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145-6154. O'Mahony, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443-445. Gilbertson, S. R.; Hoge, G. S. Tetrahedron Lett. 1998, 39, 2075-2078. Gilbertson, S. R.; Hoge, G. S.; Genov, D. G.; J. Org. Chem. 1998, 63, 10077-10080.
3. For [4 + 4] cycloadditions, see: Wender, P. A.; IhIe, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4679. Wender P. A.; Ihle, N. C.; Correia, C. R. D. J. Am. Chem. Soc. 1988, 110, 5904-5906. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. For more recent studies, see: Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suarez-Sobrino A, Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Murakami, M.; Itami, K.; Ito, Y. Synlett 1999, S1, 951-953. For [4 + 2] cycloadditions, see: Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255-1275. For more recent studies, see: Jolly, R. S.; Luedtke. G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145-6154. O'Mahony, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443-445. Gilbertson, S. R.; Hoge, G. S. Tetrahedron Lett. 1998, 39, 2075-2078. Gilbertson, S. R.; Hoge, G. S.; Genov, D. G.; J. Org. Chem. 1998, 63, 10077-10080.
4. For [4 + 4] cycloadditions, see: Wender, P. A.; IhIe, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4679. Wender P. A.; Ihle, N. C.; Correia, C. R. D. J. Am. Chem. Soc. 1988, 110, 5904-5906. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. For more recent studies, see: Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suarez-Sobrino A, Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Murakami, M.; Itami, K.; Ito, Y. Synlett 1999, S1, 951-953. For [4 + 2] cycloadditions, see: Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255-1275. For more recent studies, see: Jolly, R. S.; Luedtke. G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145-6154. O'Mahony, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443-445. Gilbertson, S. R.; Hoge, G. S. Tetrahedron Lett. 1998, 39, 2075-2078. Gilbertson, S. R.; Hoge, G. S.; Genov, D. G.; J. Org. Chem. 1998, 63, 10077-10080.
5. For [4 + 4] cycloadditions, see: Wender, P. A.; IhIe, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4679. Wender P. A.; Ihle, N. C.; Correia, C. R. D. J. Am. Chem. Soc. 1988, 110, 5904-5906. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. For more recent studies, see: Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suarez-Sobrino A, Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Murakami, M.; Itami, K.; Ito, Y. Synlett 1999, S1, 951-953. For [4 + 2] cycloadditions, see: Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255-1275. For more recent studies, see: Jolly, R. S.; Luedtke. G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145-6154. O'Mahony, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443-445. Gilbertson, S. R.; Hoge, G. S. Tetrahedron Lett. 1998, 39, 2075-2078. Gilbertson, S. R.; Hoge, G. S.; Genov, D. G.; J. Org. Chem. 1998, 63, 10077-10080.
6. For [4 + 4] cycloadditions, see: Wender, P. A.; IhIe, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4679. Wender P. A.; Ihle, N. C.; Correia, C. R. D. J. Am. Chem. Soc. 1988, 110, 5904-5906. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. For more recent studies, see: Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suarez-Sobrino A, Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Murakami, M.; Itami, K.; Ito, Y. Synlett 1999, S1, 951-953. For [4 + 2] cycloadditions, see: Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255-1275. For more recent studies, see: Jolly, R. S.; Luedtke. G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145-6154. O'Mahony, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443-445. Gilbertson, S. R.; Hoge, G. S. Tetrahedron Lett. 1998, 39, 2075-2078. Gilbertson, S. R.; Hoge, G. S.; Genov, D. G.; J. Org. Chem. 1998, 63, 10077-10080.
7. For [4 + 4] cycloadditions, see: Wender, P. A.; IhIe, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4679. Wender P. A.; Ihle, N. C.; Correia, C. R. D. J. Am. Chem. Soc. 1988, 110, 5904-5906. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. For more recent studies, see: Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suarez-Sobrino A, Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Murakami, M.; Itami, K.; Ito, Y. Synlett 1999, S1, 951-953. For [4 + 2] cycloadditions, see: Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255-1275. For more recent studies, see: Jolly, R. S.; Luedtke. G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145-6154. O'Mahony, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443-445. Gilbertson, S. R.; Hoge, G. S. Tetrahedron Lett. 1998, 39, 2075-2078. Gilbertson, S. R.; Hoge, G. S.; Genov, D. G.; J. Org. Chem. 1998, 63, 10077-10080.
8. For [4 + 4] cycloadditions, see: Wender, P. A.; IhIe, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4679. Wender P. A.; Ihle, N. C.; Correia, C. R. D. J. Am. Chem. Soc. 1988, 110, 5904-5906. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. For more recent studies, see: Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suarez-Sobrino A, Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Murakami, M.; Itami, K.; Ito, Y. Synlett 1999, S1, 951-953. For [4 + 2] cycloadditions, see: Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255-1275. For more recent studies, see: Jolly, R. S.; Luedtke. G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145-6154. O'Mahony, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443-445. Gilbertson, S. R.; Hoge, G. S. Tetrahedron Lett. 1998, 39, 2075-2078. Gilbertson, S. R.; Hoge, G. S.; Genov, D. G.; J. Org. Chem. 1998, 63, 10077-10080.
9. For [4 + 4] cycloadditions, see: Wender, P. A.; IhIe, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4679. Wender P. A.; Ihle, N. C.; Correia, C. R. D. J. Am. Chem. Soc. 1988, 110, 5904-5906. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. For more recent studies, see: Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suarez-Sobrino A, Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Murakami, M.; Itami, K.; Ito, Y. Synlett 1999, S1, 951-953. For [4 + 2] cycloadditions, see: Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255-1275. For more recent studies, see: Jolly, R. S.; Luedtke. G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145-6154. O'Mahony, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443-445. Gilbertson, S. R.; Hoge, G. S. Tetrahedron Lett. 1998, 39, 2075-2078. Gilbertson, S. R.; Hoge, G. S.; Genov, D. G.; J. Org. Chem. 1998, 63, 10077-10080.
10. For [4 + 4] cycloadditions, see: Wender, P. A.; IhIe, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4679. Wender P. A.; Ihle, N. C.; Correia, C. R. D. J. Am. Chem. Soc. 1988, 110, 5904-5906. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. For more recent studies, see: Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suarez-Sobrino A, Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Murakami, M.; Itami, K.; Ito, Y. Synlett 1999, S1, 951-953. For [4 + 2] cycloadditions, see: Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255-1275. For more recent studies, see: Jolly, R. S.; Luedtke. G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145-6154. O'Mahony, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443-445. Gilbertson, S. R.; Hoge, G. S. Tetrahedron Lett. 1998, 39, 2075-2078. Gilbertson, S. R.; Hoge, G. S.; Genov, D. G.; J. Org. Chem. 1998, 63, 10077-10080.
11. For [4 + 4] cycloadditions, see: Wender, P. A.; IhIe, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4679. Wender P. A.; Ihle, N. C.; Correia, C. R. D. J. Am. Chem. Soc. 1988, 110, 5904-5906. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. For more recent studies, see: Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suarez-Sobrino A, Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Murakami, M.; Itami, K.; Ito, Y. Synlett 1999, S1, 951-953. For [4 + 2] cycloadditions, see: Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255-1275. For more recent studies, see: Jolly, R. S.; Luedtke. G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145-6154. O'Mahony, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443-445. Gilbertson, S. R.; Hoge, G. S. Tetrahedron Lett. 1998, 39, 2075-2078. Gilbertson, S. R.; Hoge, G. S.; Genov, D. G.; J. Org. Chem. 1998, 63, 10077-10080.
12. For [4 + 4] cycloadditions, see: Wender, P. A.; IhIe, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4679. Wender P. A.; Ihle, N. C.; Correia, C. R. D. J. Am. Chem. Soc. 1988, 110, 5904-5906. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. For more recent studies, see: Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suarez-Sobrino A, Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Murakami, M.; Itami, K.; Ito, Y. Synlett 1999, S1, 951-953. For [4 + 2] cycloadditions, see: Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255-1275. For more recent studies, see: Jolly, R. S.; Luedtke. G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145-6154. O'Mahony, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443-445. Gilbertson, S. R.; Hoge, G. S. Tetrahedron Lett. 1998, 39, 2075-2078. Gilbertson, S. R.; Hoge, G. S.; Genov, D. G.; J. Org. Chem. 1998, 63, 10077-10080.
13. For [4 + 4] cycloadditions, see: Wender, P. A.; IhIe, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4679. Wender P. A.; Ihle, N. C.; Correia, C. R. D. J. Am. Chem. Soc. 1988, 110, 5904-5906. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. For more recent studies, see: Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suarez-Sobrino A, Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Murakami, M.; Itami, K.; Ito, Y. Synlett 1999, S1, 951-953. For [4 + 2] cycloadditions, see: Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255-1275. For more recent studies, see: Jolly, R. S.; Luedtke. G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145-6154. O'Mahony, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443-445. Gilbertson, S. R.; Hoge, G. S. Tetrahedron Lett. 1998, 39, 2075-2078. Gilbertson, S. R.; Hoge, G. S.; Genov, D. G.; J. Org. Chem. 1998, 63, 10077-10080.
14. For [4 + 4] cycloadditions, see: Wender, P. A.; IhIe, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4679. Wender P. A.; Ihle, N. C.; Correia, C. R. D. J. Am. Chem. Soc. 1988, 110, 5904-5906. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. For more recent studies, see: Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suarez-Sobrino A, Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Murakami, M.; Itami, K.; Ito, Y. Synlett 1999, S1, 951-953. For [4 + 2] cycloadditions, see: Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255-1275. For more recent studies, see: Jolly, R. S.; Luedtke. G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145-6154. O'Mahony, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443-445. Gilbertson, S. R.; Hoge, G. S. Tetrahedron Lett. 1998, 39, 2075-2078. Gilbertson, S. R.; Hoge, G. S.; Genov, D. G.; J. Org. Chem. 1998, 63, 10077-10080.
15. For [4 + 4] cycloadditions, see: Wender, P. A.; IhIe, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4679. Wender P. A.; Ihle, N. C.; Correia, C. R. D. J. Am. Chem. Soc. 1988, 110, 5904-5906. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. For more recent studies, see: Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suarez-Sobrino A, Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Murakami, M.; Itami, K.; Ito, Y. Synlett 1999, S1, 951-953. For [4 + 2] cycloadditions, see: Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255-1275. For more recent studies, see: Jolly, R. S.; Luedtke. G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145-6154. O'Mahony, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443-445. Gilbertson, S. R.; Hoge, G. S. Tetrahedron Lett. 1998, 39, 2075-2078. Gilbertson, S. R.; Hoge, G. S.; Genov, D. G.; J. Org. Chem. 1998, 63, 10077-10080.
16. For intramolecular [5 + 2] cycloadditions with alkynes, see: Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721. For more recent reports, see: Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Kadereit, D.; Love, J. A.; Rieck, H. J. Am. Chem. Soc. 1999, 121, 10442-10443. Wender, P. A.; Dyckman, A. J. Org. Lett. 1999, 1, 2089-2092. Trost, B. M.; Toste, F. D.; Shen, H. J. Am. Chem. Soc. 2000, 122, 2379-2380. For intermolecular [5 + 2] cycloadditions with alkynes, see: Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976-10977. Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Scanio, M. J. C. Org. Lett. 2000, 2, 1609-1611. For intramolecular [5 + 2] cycloadditions with alkenes, see: Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940-1941. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A.; Pleuss, N. Tetrahedron 1998, 54, 7203-7220. For intramolecular [5 + 2] cycloadditions with allenes, see: Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1999, 121, 5348-5349. Wender, P. A.; Fuji, M.; Husfeld, C. O.; Love, J. A. Org. Lett. 1999, 1, 137-139.
17. For intramolecular [5 + 2] cycloadditions with alkynes, see: Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721. For more recent reports, see: Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Kadereit, D.; Love, J. A.; Rieck, H. J. Am. Chem. Soc. 1999, 121, 10442-10443. Wender, P. A.; Dyckman, A. J. Org. Lett. 1999, 1, 2089-2092. Trost, B. M.; Toste, F. D.; Shen, H. J. Am. Chem. Soc. 2000, 122, 2379-2380. For intermolecular [5 + 2] cycloadditions with alkynes, see: Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976-10977. Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Scanio, M. J. C. Org. Lett. 2000, 2, 1609-1611. For intramolecular [5 + 2] cycloadditions with alkenes, see: Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940-1941. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A.; Pleuss, N. Tetrahedron 1998, 54, 7203-7220. For intramolecular [5 + 2] cycloadditions with allenes, see: Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1999, 121, 5348-5349. Wender, P. A.; Fuji, M.; Husfeld, C. O.; Love, J. A. Org. Lett. 1999, 1, 137-139.
18. For intramolecular [5 + 2] cycloadditions with alkynes, see: Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721. For more recent reports, see: Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Kadereit, D.; Love, J. A.; Rieck, H. J. Am. Chem. Soc. 1999, 121, 10442-10443. Wender, P. A.; Dyckman, A. J. Org. Lett. 1999, 1, 2089-2092. Trost, B. M.; Toste, F. D.; Shen, H. J. Am. Chem. Soc. 2000, 122, 2379-2380. For intermolecular [5 + 2] cycloadditions with alkynes, see: Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976-10977. Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Scanio, M. J. C. Org. Lett. 2000, 2, 1609-1611. For intramolecular [5 + 2] cycloadditions with alkenes, see: Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940-1941. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A.; Pleuss, N. Tetrahedron 1998, 54, 7203-7220. For intramolecular [5 + 2] cycloadditions with allenes, see: Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1999, 121, 5348-5349. Wender, P. A.; Fuji, M.; Husfeld, C. O.; Love, J. A. Org. Lett. 1999, 1, 137-139.
19. For intramolecular [5 + 2] cycloadditions with alkynes, see: Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721. For more recent reports, see: Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Kadereit, D.; Love, J. A.; Rieck, H. J. Am. Chem. Soc. 1999, 121, 10442-10443. Wender, P. A.; Dyckman, A. J. Org. Lett. 1999, 1, 2089-2092. Trost, B. M.; Toste, F. D.; Shen, H. J. Am. Chem. Soc. 2000, 122, 2379-2380. For intermolecular [5 + 2] cycloadditions with alkynes, see: Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976-10977. Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Scanio, M. J. C. Org. Lett. 2000, 2, 1609-1611. For intramolecular [5 + 2] cycloadditions with alkenes, see: Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940-1941. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A.; Pleuss, N. Tetrahedron 1998, 54, 7203-7220. For intramolecular [5 + 2] cycloadditions with allenes, see: Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1999, 121, 5348-5349. Wender, P. A.; Fuji, M.; Husfeld, C. O.; Love, J. A. Org. Lett. 1999, 1, 137-139.
20. For intramolecular [5 + 2] cycloadditions with alkynes, see: Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721. For more recent reports, see: Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Kadereit, D.; Love, J. A.; Rieck, H. J. Am. Chem. Soc. 1999, 121, 10442-10443. Wender, P. A.; Dyckman, A. J. Org. Lett. 1999, 1, 2089-2092. Trost, B. M.; Toste, F. D.; Shen, H. J. Am. Chem. Soc. 2000, 122, 2379-2380. For intermolecular [5 + 2] cycloadditions with alkynes, see: Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976-10977. Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Scanio, M. J. C. Org. Lett. 2000, 2, 1609-1611. For intramolecular [5 + 2] cycloadditions with alkenes, see: Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940-1941. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A.; Pleuss, N. Tetrahedron 1998, 54, 7203-7220. For intramolecular [5 + 2] cycloadditions with allenes, see: Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1999, 121, 5348-5349. Wender, P. A.; Fuji, M.; Husfeld, C. O.; Love, J. A. Org. Lett. 1999, 1, 137-139.
21. For intramolecular [5 + 2] cycloadditions with alkynes, see: Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721. For more recent reports, see: Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Kadereit, D.; Love, J. A.; Rieck, H. J. Am. Chem. Soc. 1999, 121, 10442-10443. Wender, P. A.; Dyckman, A. J. Org. Lett. 1999, 1, 2089-2092. Trost, B. M.; Toste, F. D.; Shen, H. J. Am. Chem. Soc. 2000, 122, 2379-2380. For intermolecular [5 + 2] cycloadditions with alkynes, see: Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976-10977. Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Scanio, M. J. C. Org. Lett. 2000, 2, 1609-1611. For intramolecular [5 + 2] cycloadditions with alkenes, see: Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940-1941. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A.; Pleuss, N. Tetrahedron 1998, 54, 7203-7220. For intramolecular [5 + 2] cycloadditions with allenes, see: Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1999, 121, 5348-5349. Wender, P. A.; Fuji, M.; Husfeld, C. O.; Love, J. A. Org. Lett. 1999, 1, 137-139.
22. For intramolecular [5 + 2] cycloadditions with alkynes, see: Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721. For more recent reports, see: Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Kadereit, D.; Love, J. A.; Rieck, H. J. Am. Chem. Soc. 1999, 121, 10442-10443. Wender, P. A.; Dyckman, A. J. Org. Lett. 1999, 1, 2089-2092. Trost, B. M.; Toste, F. D.; Shen, H. J. Am. Chem. Soc. 2000, 122, 2379-2380. For intermolecular [5 + 2] cycloadditions with alkynes, see: Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976-10977. Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Scanio, M. J. C. Org. Lett. 2000, 2, 1609-1611. For intramolecular [5 + 2] cycloadditions with alkenes, see: Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940-1941. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A.; Pleuss, N. Tetrahedron 1998, 54, 7203-7220. For intramolecular [5 + 2] cycloadditions with allenes, see: Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1999, 121, 5348-5349. Wender, P. A.; Fuji, M.; Husfeld, C. O.; Love, J. A. Org. Lett. 1999, 1, 137-139.
23. For intramolecular [5 + 2] cycloadditions with alkynes, see: Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721. For more recent reports, see: Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Kadereit, D.; Love, J. A.; Rieck, H. J. Am. Chem. Soc. 1999, 121, 10442-10443. Wender, P. A.; Dyckman, A. J. Org. Lett. 1999, 1, 2089-2092. Trost, B. M.; Toste, F. D.; Shen, H. J. Am. Chem. Soc. 2000, 122, 2379-2380. For intermolecular [5 + 2] cycloadditions with alkynes, see: Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976-10977. Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Scanio, M. J. C. Org. Lett. 2000, 2, 1609-1611. For intramolecular [5 + 2] cycloadditions with alkenes, see: Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940-1941. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A.; Pleuss, N. Tetrahedron 1998, 54, 7203-7220. For intramolecular [5 + 2] cycloadditions with allenes, see: Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1999, 121, 5348-5349. Wender, P. A.; Fuji, M.; Husfeld, C. O.; Love, J. A. Org. Lett. 1999, 1, 137-139.
24. For intramolecular [5 + 2] cycloadditions with alkynes, see: Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721. For more recent reports, see: Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Kadereit, D.; Love, J. A.; Rieck, H. J. Am. Chem. Soc. 1999, 121, 10442-10443. Wender, P. A.; Dyckman, A. J. Org. Lett. 1999, 1, 2089-2092. Trost, B. M.; Toste, F. D.; Shen, H. J. Am. Chem. Soc. 2000, 122, 2379-2380. For intermolecular [5 + 2] cycloadditions with alkynes, see: Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976-10977. Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Scanio, M. J. C. Org. Lett. 2000, 2, 1609-1611. For intramolecular [5 + 2] cycloadditions with alkenes, see: Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940-1941. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A.; Pleuss, N. Tetrahedron 1998, 54, 7203-7220. For intramolecular [5 + 2] cycloadditions with allenes, see: Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1999, 121, 5348-5349. Wender, P. A.; Fuji, M.; Husfeld, C. O.; Love, J. A. Org. Lett. 1999, 1, 137-139.
25. For intramolecular [5 + 2] cycloadditions with alkynes, see: Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721. For more recent reports, see: Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Kadereit, D.; Love, J. A.; Rieck, H. J. Am. Chem. Soc. 1999, 121, 10442-10443. Wender, P. A.; Dyckman, A. J. Org. Lett. 1999, 1, 2089-2092. Trost, B. M.; Toste, F. D.; Shen, H. J. Am. Chem. Soc. 2000, 122, 2379-2380. For intermolecular [5 + 2] cycloadditions with alkynes, see: Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976-10977. Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Scanio, M. J. C. Org. Lett. 2000, 2, 1609-1611. For intramolecular [5 + 2] cycloadditions with alkenes, see: Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940-1941. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A.; Pleuss, N. Tetrahedron 1998, 54, 7203-7220. For intramolecular [5 + 2] cycloadditions with allenes, see: Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1999, 121, 5348-5349. Wender, P. A.; Fuji, M.; Husfeld, C. O.; Love, J. A. Org. Lett. 1999, 1, 137-139.
26. Wender, P. A.; Correa, A. G.; Sato. Y.; Sun, R. J. Am. Chem. Soc. In press.
27. Nishizawa, M.; Inoue, A.; Hayashi, Y.; Satrapradja. S.; Kosela, S.; Iwashita, T. J. Org. Chem. 1984, 49, 3660-3662.
28. (a) Mehta, G.; Krishnamurthy, N.; Karra, S. R. J. Am. Chem. Soc. 1991, 113, 5765-5775.
29. (b) Hanssen, T.; Wickberg, B. J. Org. Chem. 1992, 57, 5370-5376.
30. (c) Harmata, M.: Carter, K. W. Tetrahedron Lett. 1997, 38, 7985-7988.
31. Kitahara, T.; Mori, K. J. Org. Chem. 1984, 49, 3281-3285.
32. Suffert, J.; Toussaint, D. J. Org. Chem. 1995, 60, 3550-3553.
33. Steglich, W.; Höfle, G. Angew. Chem., Intl. Ed. Engl. 1969, 8, 981.
34. Rona, P.; Crabbé. P. J. Am. Chem. Soc. 1969, 91, 3289-3292.
35. Petasis, N. A.; Hu, Y.-H. J. Org. Chem. 1997, 62, 782-783.
36. Wright, M. E.; Allred, G. D. J. Org. Chem. 1993, 58, 4122-4126.
37. Another approach called for a saponification of the aldol adduct 8 and subsequent treatment of the product with dimethyl DMF acetal to effect a decarboxylation elimination to produce 10. However, various saponification conditions gave either no reaction or induced a retro-aldol reaction. (Equation presented)
38. An alternative mechanism would be the formation of a β-lactone by the attack of the free acid on the acetate, followed by a decarboxylation reaction.
39. No reaction occurred with Wilkinson's catalyst. Wilkinson's catalyst with AgOTf as additive caused fast isomerization of the allene to produce dienes.
40. Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63, 4164-4165.
41. We have previously proposed two general mechanistic classes for the [5 + 2] cycloaddition which are differentiated by the timing of cyclopropane opening and CC bond formation. For space consideration, only one is partially illustrated here, that being a path in which CC bond formation precedes cyclopropane cleavage. For additional discussion on the mechanism, see ref 2.
42. 4, gave sluggish reactions with poor conversions, presumably due to the steric hindrance of the alkene.
43. Mori, K.; Tomioka, H.; Fukuyo, E.; Yanagi, K. Liebigs Ann. Chem. 1993, 6, 671-682.