Asymmetric Synthesis of the Tricyclic Core of NGF-Inducing Cyathane Diterpenes via a Transition-Metal-Catalyzed [5 + 2] Cycloaddition

Organic Letters

Volumn 3, Issue 13, 2001, Pages 2105-2108

  Wender, Paul A ^a   Christopher Bi, F ^a   Brodney, Michael A ^a   Gosselin, Francis ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLOCYATHIN; CYCLOHEXENE DERIVATIVE; DITERPENE; LIMONENE; NERVE GROWTH FACTOR; SCABRONINE E; TERPENE;

ARTICLE; CHEMISTRY; DRUG EFFECT; METABOLISM; SYNTHESIS;

CYCLOHEXENES; DITERPENES; NERVE GROWTH FACTOR; TERPENES;

EID: 0035963703     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0160699     Document Type: Article

References (71)

1. For [4 + 4] cycloadditions, see: Wender, P. A.; Ihle, N. C. J. Am. l Chem. Soc. 1986, 108, 4678-4674. 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. Våabera, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4904. 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. Cliem. 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, 2075-2178. 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.; Ihle, N. C. J. Am. l Chem. Soc. 1986, 108, 4678-4674. 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. Våabera, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4904. 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. Cliem. 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, 2075-2178. 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.; Ihle, N. C. J. Am. l Chem. Soc. 1986, 108, 4678-4674. 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. Våabera, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4904. 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. Cliem. 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, 2075-2178. 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.; Ihle, N. C. J. Am. l Chem. Soc. 1986, 108, 4678-4674. 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. Våabera, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4904. 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. Cliem. 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, 2075-2178. 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.; Ihle, N. C. J. Am. l Chem. Soc. 1986, 108, 4678-4674. 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. Våabera, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4904. 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. Cliem. 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, 2075-2178. 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.; Ihle, N. C. J. Am. l Chem. Soc. 1986, 108, 4678-4674. 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. Våabera, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4904. 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. Cliem. 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, 2075-2178. 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.; Ihle, N. C. J. Am. l Chem. Soc. 1986, 108, 4678-4674. 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. Våabera, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4904. 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. Cliem. 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, 2075-2178. 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.; Ihle, N. C. J. Am. l Chem. Soc. 1986, 108, 4678-4674. 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. Våabera, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4904. 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. Cliem. 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, 2075-2178. 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.; Ihle, N. C. J. Am. l Chem. Soc. 1986, 108, 4678-4674. 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. Våabera, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4904. 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. Cliem. 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, 2075-2178. 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.; Ihle, N. C. J. Am. l Chem. Soc. 1986, 108, 4678-4674. 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. Våabera, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4904. 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. Cliem. 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, 2075-2178. 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.; Ihle, N. C. J. Am. l Chem. Soc. 1986, 108, 4678-4674. 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. Våabera, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4904. 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. Cliem. 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, 2075-2178. 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.; Ihle, N. C. J. Am. l Chem. Soc. 1986, 108, 4678-4674. 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. Våabera, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4904. 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. Cliem. 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, 2075-2178. 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.; Ihle, N. C. J. Am. l Chem. Soc. 1986, 108, 4678-4674. 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. Våabera, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4904. 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. Cliem. 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, 2075-2178. 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.; Ihle, N. C. J. Am. l Chem. Soc. 1986, 108, 4678-4674. 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. Våabera, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4904. 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. Cliem. 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, 2075-2178. 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.; Ihle, N. C. J. Am. l Chem. Soc. 1986, 108, 4678-4674. 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. Våabera, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4904. 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. Cliem. 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, 2075-2178. 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: (a) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem.Soc. 1995, 117, 4720-4721.
17. For more recent reports, see: (b) Wender, P. A,; Dyckman, A. J.; Husfeld, C. O.; Kadereit, D.; Love, J. A.; Rieck, H. J .Am. Chem. Soc. 1999, 121, 1044-10443. Wender, P. A.; Dyckman, A. J. Org. Lett. 1999, 1, 2089-2092.
18. For more recent reports, see: (b) Wender, P. A,; Dyckman, A. J.; Husfeld, C. O.; Kadereit, D.; Love, J. A.; Rieck, H. J .Am. Chem. Soc. 1999, 121, 1044-10443. Wender, P. A.; Dyckman, A. J. Org. Lett. 1999, 1, 2089-2092.
19. For intermolecular [5 + 2] cycloadditions with alkynes, see: (c) Wender, P. A.; Rieck, H,; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976-10977.
20. Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Scnio, M. J. C. Org. Lett. 2000, 2, 1609-1611.
21. Wender, P. A.; Barzilay, C. M.; Dyckman, A. J. J. Am. Chem. Soc. 2001, 123, 179-180.
22. For intramolecular [5 + 2] cycloadditions with alkenes, see: (d) 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.
23. For intramolecular [5 + 2] cycloadditions with alkenes, see: (d) 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.
24. For intramolecular [5 + 2] cycloadditions with allenes, see: (e) 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. Wender, P. A.; Zhang, L. Org. Lett. 2000, 2, 2323-2326.
25. For intramolecular [5 + 2] cycloadditions with allenes, see: (e) 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. Wender, P. A.; Zhang, L. Org. Lett. 2000, 2, 2323-2326.
26. For intramolecular [5 + 2] cycloadditions with allenes, see: (e) 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. Wender, P. A.; Zhang, L. Org. Lett. 2000, 2, 2323-2326.
27. For more recent studies using other catalysts, see: (f) Wender, P. A.; Sperandio, D. A. J. Org. Chem. 1998, 63, 4164-4165.
28. (g) Trost, B. M.; Toste, F. D.; Shen, H. J. Am. Chem. Soc. 2000, 122, 2379-2380.
29. Wender, P. A.; Correa, A. G.; Sato, Y.; Sun, R. J. Am. Chem. Soc. 2000, 122, 7815-7816.
30. (a) Ayer, W. A.; Taube, H. Tetrahedron Lett. 1972, 1917-1920.
31. (b) Ayer. W. A.; Taube, H. Can. J. Chem. 1973, 51, 3842-3854.
32. (c) Brodie, H. J. Can. J. Bot. 1966, 44, 1235-1237.
33. Allbutt, A. D.; Ayer, W. A.; Brodie, H. J.; Johri, B. N.; Taube, H. Can. J. Microbiol. 1971, 17, 1401-1407.
34. For the isolation of erinacines A-C, see: Kawagishi, H.; Shimada, A.; Shirai, R.; Okamoto, K.; Ojima, F.; Sakamoto, H.; Ishiguro, Y.; Furukawa, S. Tetrahedron Lett. 1994, 35, 1569-1572. For Erinacine D, see: Kawagishi, H.; Shimada, A.; Shizuki, K.; Mori, H.; Okamoto, K.; Sakamoto, H.; Furukawa, S. Heterocycl. Commun. 1996, 2, 51-54. For erinacines E-G, see: Kawagishi, H.; Shimada, A.; Satoshi, H.; Hironobu, M.; Sakamoto, H.; Ishiguro, Y.; Sakemi, S.; Bordner, J.; Kojim, N.; Furukawa, S. Tetrahedron Lett. 1996, 37, 7399-7402. For the isolation of erinacine P, see: Kenmoku, H.; Sassa, T.; Kato, N. Tetrahedron Lett. 2000, 41, 4389-4393.
35. For the isolation of erinacines A-C, see: Kawagishi, H.; Shimada, A.; Shirai, R.; Okamoto, K.; Ojima, F.; Sakamoto, H.; Ishiguro, Y.; Furukawa, S. Tetrahedron Lett. 1994, 35, 1569-1572. For Erinacine D, see: Kawagishi, H.; Shimada, A.; Shizuki, K.; Mori, H.; Okamoto, K.; Sakamoto, H.; Furukawa, S. Heterocycl. Commun. 1996, 2, 51-54. For erinacines E-G, see: Kawagishi, H.; Shimada, A.; Satoshi, H.; Hironobu, M.; Sakamoto, H.; Ishiguro, Y.; Sakemi, S.; Bordner, J.; Kojim, N.; Furukawa, S. Tetrahedron Lett. 1996, 37, 7399-7402. For the isolation of erinacine P, see: Kenmoku, H.; Sassa, T.; Kato, N. Tetrahedron Lett. 2000, 41, 4389-4393.
36. For the isolation of erinacines A-C, see: Kawagishi, H.; Shimada, A.; Shirai, R.; Okamoto, K.; Ojima, F.; Sakamoto, H.; Ishiguro, Y.; Furukawa, S. Tetrahedron Lett. 1994, 35, 1569-1572. For Erinacine D, see: Kawagishi, H.; Shimada, A.; Shizuki, K.; Mori, H.; Okamoto, K.; Sakamoto, H.; Furukawa, S. Heterocycl. Commun. 1996, 2, 51-54. For erinacines E-G, see: Kawagishi, H.; Shimada, A.; Satoshi, H.; Hironobu, M.; Sakamoto, H.; Ishiguro, Y.; Sakemi, S.; Bordner, J.; Kojim, N.; Furukawa, S. Tetrahedron Lett. 1996, 37, 7399-7402. For the isolation of erinacine P, see: Kenmoku, H.; Sassa, T.; Kato, N. Tetrahedron Lett. 2000, 41, 4389-4393.
37. For the isolation of erinacines A-C, see: Kawagishi, H.; Shimada, A.; Shirai, R.; Okamoto, K.; Ojima, F.; Sakamoto, H.; Ishiguro, Y.; Furukawa, S. Tetrahedron Lett. 1994, 35, 1569-1572. For Erinacine D, see: Kawagishi, H.; Shimada, A.; Shizuki, K.; Mori, H.; Okamoto, K.; Sakamoto, H.; Furukawa, S. Heterocycl. Commun. 1996, 2, 51-54. For erinacines E-G, see: Kawagishi, H.; Shimada, A.; Satoshi, H.; Hironobu, M.; Sakamoto, H.; Ishiguro, Y.; Sakemi, S.; Bordner, J.; Kojim, N.; Furukawa, S. Tetrahedron Lett. 1996, 37, 7399-7402. For the isolation of erinacine P, see: Kenmoku, H.; Sassa, T.; Kato, N. Tetrahedron Lett. 2000, 41, 4389-4393.
38. For scabronine A, see: Ohta, T.; Kita, T.; Kobayashi, N.; Obara, Y.; Nakahata, N.; Ohizumi, Y.; Takaya, Y.; Oshima, Y. Tetrahedron Lett. 1998, 39, 6229-6232. For scabronines B-F, see: Kita, T.; Takaya, Y.; Oshima, Y.; Ohta, T.; Aizawa, K.; Hirano, T.; Inakuma, T. Tetrahedron 1998, 54, 11877-11886.
39. For scabronine A, see: Ohta, T.; Kita, T.; Kobayashi, N.; Obara, Y.; Nakahata, N.; Ohizumi, Y.; Takaya, Y.; Oshima, Y. Tetrahedron Lett. 1998, 39, 6229-6232. For scabronines B-F, see: Kita, T.; Takaya, Y.; Oshima, Y.; Ohta, T.; Aizawa, K.; Hirano, T.; Inakuma, T. Tetrahedron 1998, 54, 11877-11886.
40. (a) Greene, L. A.; Shooter, E. M. Annu. Rev. Neurosci. 1980, 3, 353-402.
41. (b) Yankner, B. A.; Shooter, E. M. Annu. Rev. Biochem. 1982, 51, 845-868.
42. Dijkhuizen, P. A.; Verhaagen, J. Neuro. Res. Commun. 1999, 24, 1-10.
43. (a) Rosenberg, S. Annu. Rep. Med. Chem. 1992, 27, 41-48.
44. (b) Bigge, C. F.; Boxer, P. A. Annu. Rep. Med. Chem. 1994, 29, 13-22.
45. (c) Saragovi, H. U.; Burgess, K. Exp. Opin. Ther. Patents 1999, 9, 737-751.
46. Reviewed in: Wright, D. L.; Whitehead, C. R. Org. Prep. Proc. Int. 2000, 32, 307-330.
47. For total syntheses of cyathane diterpenes, see: (a) Snider, B. B.; Vo, N. H.; O'Neil, S. V.; Foxman, B. M. J. Am. Chem. Soc. 1996, 118, 7644-7645.
48. (b) Tori, M.; Toyoda, N.; Sono, S. J. Org. Chem, 1998, 63, 306-313.
49. (c) Piers, E.; Gilbert, M.; Cook, K. L. Org. Lett. 2000, 2, 1407-1410.
50. (d) Ward, D. E.; Gai, Y. Z.; Qiao, Q. Org. Lett. 2000, 2, 2125-2127.
51. For synthetic approaches to cyathanes, see: (a) Ayer, W. A.; Ward, D. E.; Browne, L. M.; Delbaere, L. T.; Hoyano, Y. Can. J. Chem. 1981, 59, 2665-2672.
52. (b) Ward, D. E. Can. J. Chem. 1987, 65, 2380-2384.
53. (c) Paquette, L. A.; Dahnke, K. R. J. Org. Chem. 1994, 59, 885-899.
54. (d) Magnus, P.; Shen, L. Tetrahedron 1999, 55, 3553-3560.
55. (e) Wright, D. L.; Whitehead, C. R.; Sessions, H.; Ghiviriga, I.; Frey, D. A. Org. Lett. 1999, 1, 1535-1538.
56. (f) Takeda, K.; Nakane, D.; Takeda, M. Org. Lett. 2000, 2, 1903-1905.
57. (a) van Tamelen, E. E.; Milne, G. M.; Suffness, M. I.; Rudler Chauvin, M. C.; Anderson, R. J.; Achini, R. S. J. Am. Chem. Soc. 1970, 92, 7202-7204.
58. (b) Lange, G. L.; Neidenrt E. E.; Orrom, W. J.; Wallace, D. J. Can. J. Chem. 1978, 56, 1628-1633.
59. (c) White, J. D.; Ruppert, J. F.; Avery M. A.; Torn, S.; Nokami, J. J. Am. Chem. Soc. 1981, 103, 1813-1821.
60. (d) Mehta, G.; Krishnamurthy, N. Tetrahedron Lett. 1987, 28, 5945-5948.
61. (e) Wright, J.; Drtina, G. J.; Roberts, R. A.; Raquette, L. A. J. Am. Chem. Soc. 1988. 110, 5806-5817.
62. (f) Paquette, L. A.; Kang, H.-J. J. Am. Chem. Soc. 1990, 112, 3252-3253.
63. (g) Mehta, G.; Krishnamurthy, N.; Karra, R. S. J. Am. Chem. Soc. 1991, 113, 5765-5775.
64. Pappo, R.: Allen, D. S., Jr.; Lemieux, R. U.; Johnson, W. S. J. Org. Chem. 1956, 21, 478-479.
65. Imamoto, T.; Takiyama, N.; Nakamura, K.; Hatajima, T.; Kamiya, Y. J. Am. Chem. Soc. 1989, 111, 4392-4398.
66. Corey, E. J.; Katzenellenbogen, J. A.; Posner, G. A. J. Am. Chem. Soc. 1967, 89, 4245-4247.
67. Only major diastereomer 8 (isolated in 69% yield) was carried on to test the feasibility of the key cycloaddition.
68. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155-4156.
69. 2: C. 79.12; H, 9.78. Found: C: 79.05; H: 9.71.
70. 2 = 0.085 for all data; GOF = 1.17. The author has deposited the atomic coordinates for the structure of 13 with the Cambridge Crystallographic Data Center, 12 Union Road, Cambodge, CB2 1EZ, U.K.
71. For a more detailed mechanistic interpretation see, for example, ref 2b.