A concise asymmetric route to the bridged bicyclic tropane alkaloid ferruginine using enyne ring-closing metathesis

Organic Letters

Volumn 6, Issue 9, 2004, Pages 1469-1471

  Aggarwal, Varinder K ^a   Astle, Christopher J ^a   Rogers Evans, Mark ^a,b  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b F HOFFMANN LA ROCHE LTD   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; FERRUGININE; TROPANE ALKALOID; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; RING CLOSING METATHESIS; SYNTHESIS;

ALKYNES; BICYCLO COMPOUNDS, HETEROCYCLIC; CATALYSIS; MOLECULAR CONFORMATION; OXIDATION-REDUCTION;

EID: 2442490954     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049665m     Document Type: Article

References (47)

1. For a general review, see: Lounasmaa, M.; Tamminen, T. The Alkaloids, The Tropane Alkaloids; Academic Press: New York, 1993; Vol. 44, pp 1-114.
2. Swanson, K. L.; Albuquerque, E. X. Handb. Exp. Pharmacol. 1992, 102, 620-621.
3. For reviews of RCM, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388. (c) Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (d) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043. (e) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077. (f) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29. (e) Semeril, D.; Bruneau, C.; Dixneuf, P. H. Adv. Synth. Catal. 2002, 344, 585-595. (h) Poulsen, C. S.; Madsen, R. Synthesis 2003, 1, 1-18. (i) Hoveyda A. H.; Gillingham D. G.; Van Veldhuizen J. J.; Kataoka O.; Garber S. B.; Kingsbury J. S.; Harrity J. P. A. Org. Biomol. Chem. 2004, 2, 8-23.
4. For reviews of RCM, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388. (c) Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (d) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043. (e) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077. (f) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29. (e) Semeril, D.; Bruneau, C.; Dixneuf, P. H. Adv. Synth. Catal. 2002, 344, 585-595. (h) Poulsen, C. S.; Madsen, R. Synthesis 2003, 1, 1-18. (i) Hoveyda A. H.; Gillingham D. G.; Van Veldhuizen J. J.; Kataoka O.; Garber S. B.; Kingsbury J. S.; Harrity J. P. A. Org. Biomol. Chem. 2004, 2, 8-23.
5. For reviews of RCM, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388. (c) Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (d) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043. (e) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077. (f) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29. (e) Semeril, D.; Bruneau, C.; Dixneuf, P. H. Adv. Synth. Catal. 2002, 344, 585-595. (h) Poulsen, C. S.; Madsen, R. Synthesis 2003, 1, 1-18. (i) Hoveyda A. H.; Gillingham D. G.; Van Veldhuizen J. J.; Kataoka O.; Garber S. B.; Kingsbury J. S.; Harrity J. P. A. Org. Biomol. Chem. 2004, 2, 8-23.
6. For reviews of RCM, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388. (c) Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (d) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043. (e) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077. (f) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29. (e) Semeril, D.; Bruneau, C.; Dixneuf, P. H. Adv. Synth. Catal. 2002, 344, 585-595. (h) Poulsen, C. S.; Madsen, R. Synthesis 2003, 1, 1-18. (i) Hoveyda A. H.; Gillingham D. G.; Van Veldhuizen J. J.; Kataoka O.; Garber S. B.; Kingsbury J. S.; Harrity J. P. A. Org. Biomol. Chem. 2004, 2, 8-23.
7. For reviews of RCM, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388. (c) Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (d) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043. (e) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077. (f) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29. (e) Semeril, D.; Bruneau, C.; Dixneuf, P. H. Adv. Synth. Catal. 2002, 344, 585-595. (h) Poulsen, C. S.; Madsen, R. Synthesis 2003, 1, 1-18. (i) Hoveyda A. H.; Gillingham D. G.; Van Veldhuizen J. J.; Kataoka O.; Garber S. B.; Kingsbury J. S.; Harrity J. P. A. Org. Biomol. Chem. 2004, 2, 8-23.
8. For reviews of RCM, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388. (c) Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (d) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043. (e) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077. (f) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29. (e) Semeril, D.; Bruneau, C.; Dixneuf, P. H. Adv. Synth. Catal. 2002, 344, 585-595. (h) Poulsen, C. S.; Madsen, R. Synthesis 2003, 1, 1-18. (i) Hoveyda A. H.; Gillingham D. G.; Van Veldhuizen J. J.; Kataoka O.; Garber S. B.; Kingsbury J. S.; Harrity J. P. A. Org. Biomol. Chem. 2004, 2, 8-23.
9. For reviews of RCM, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388. (c) Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (d) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043. (e) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077. (f) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29. (e) Semeril, D.; Bruneau, C.; Dixneuf, P. H. Adv. Synth. Catal. 2002, 344, 585-595. (h) Poulsen, C. S.; Madsen, R. Synthesis 2003, 1, 1-18. (i) Hoveyda A. H.; Gillingham D. G.; Van Veldhuizen J. J.; Kataoka O.; Garber S. B.; Kingsbury J. S.; Harrity J. P. A. Org. Biomol. Chem. 2004, 2, 8-23.
10. For reviews of RCM, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388. (c) Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (d) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043. (e) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077. (f) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29. (e) Semeril, D.; Bruneau, C.; Dixneuf, P. H. Adv. Synth. Catal. 2002, 344, 585-595. (h) Poulsen, C. S.; Madsen, R. Synthesis 2003, 1, 1-18. (i) Hoveyda A. H.; Gillingham D. G.; Van Veldhuizen J. J.; Kataoka O.; Garber S. B.; Kingsbury J. S.; Harrity J. P. A. Org. Biomol. Chem. 2004, 2, 8-23.
11. For reviews of RCM, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388. (c) Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (d) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043. (e) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077. (f) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29. (e) Semeril, D.; Bruneau, C.; Dixneuf, P. H. Adv. Synth. Catal. 2002, 344, 585-595. (h) Poulsen, C. S.; Madsen, R. Synthesis 2003, 1, 1-18. (i) Hoveyda A. H.; Gillingham D. G.; Van Veldhuizen J. J.; Kataoka O.; Garber S. B.; Kingsbury J. S.; Harrity J. P. A. Org. Biomol. Chem. 2004, 2, 8-23.
12. Neipp, C. E.; Martin, S. F. J. Org. Chem. 2003, 68, 8867-8878 and references therein.
13. For a review, see: Hoffman, R. W. Chem. Rev. 1989, 89, 1841-1860.
14. Neipp, C. E.; Martin, S. F. Tetrahedron Lett. 2002, 43, 1779-1782.
15. Although this reaction has been described to furnish a 95:5 (cis:trans) ratio of diastereomers we have not been able to reproduce this result (80: 20, cis:trans obtained). See: (a) Shono, T.; Fujita, T.; Matsumura, Y. Chem. Lett. 1991, 81-84. (b) Ma, D.; Yang, J. J. Am. Chem. Soc. 2001, 123, 9706-9707. Other workers have also reported levels of selectivity similar to our own. See: (c) Chiesa, M. V.; Manzoni, L.; Scalastico, C. Synlett 1996, 441-443. (d) Beal, L. M.; Moeller, K. D. Tetrahedron Lett. 1998, 39, 4639-4642. (e) Grossmith, C. E.; Senia, F.; Wagner, J. Synlett 1999, 10, 1660-1662. (f) Mulzer, J.; Schulzchen, F.; Bats, J.-W. Tetrahedron 2000, 56, 4289-4298. (g) Tong, Y.; Forbian, Y. M.; Wu, M.; Boyd, N. D.; Moeller, K. D. J. Org. Chem. 2000, 65, 2484-2493. (h) Manzoni, L.; Colombo, M.; May, E.; Scolastico, C. Tetrahedron 2001, 57, 249-255. (i) Zhang, X.; Schmitt, A. C.; Jiang, W. Tetrahedron Lett. 2001, 42, 5335-5338. (j) Kim, S.; Hayashi, K.; Kitano, Y.; Tada, M.; Chiba, K. Org. Lett. 2002, 4, 3735-3737. (k) Harris, P. W. R.; Brimble, M. A.; Gluckman, P. D. Org. Lett. 2003, 5, 1847-1850.
16. Although this reaction has been described to furnish a 95:5 (cis:trans) ratio of diastereomers we have not been able to reproduce this result (80: 20, cis:trans obtained). See: (a) Shono, T.; Fujita, T.; Matsumura, Y. Chem. Lett. 1991, 81-84. (b) Ma, D.; Yang, J. J. Am. Chem. Soc. 2001, 123, 9706-9707. Other workers have also reported levels of selectivity similar to our own. See: (c) Chiesa, M. V.; Manzoni, L.; Scalastico, C. Synlett 1996, 441-443. (d) Beal, L. M.; Moeller, K. D. Tetrahedron Lett. 1998, 39, 4639-4642. (e) Grossmith, C. E.; Senia, F.; Wagner, J. Synlett 1999, 10, 1660-1662. (f) Mulzer, J.; Schulzchen, F.; Bats, J.-W. Tetrahedron 2000, 56, 4289-4298. (g) Tong, Y.; Forbian, Y. M.; Wu, M.; Boyd, N. D.; Moeller, K. D. J. Org. Chem. 2000, 65, 2484-2493. (h) Manzoni, L.; Colombo, M.; May, E.; Scolastico, C. Tetrahedron 2001, 57, 249-255. (i) Zhang, X.; Schmitt, A. C.; Jiang, W. Tetrahedron Lett. 2001, 42, 5335-5338. (j) Kim, S.; Hayashi, K.; Kitano, Y.; Tada, M.; Chiba, K. Org. Lett. 2002, 4, 3735-3737. (k) Harris, P. W. R.; Brimble, M. A.; Gluckman, P. D. Org. Lett. 2003, 5, 1847-1850.
17. Although this reaction has been described to furnish a 95:5 (cis:trans) ratio of diastereomers we have not been able to reproduce this result (80: 20, cis:trans obtained). See: (a) Shono, T.; Fujita, T.; Matsumura, Y. Chem. Lett. 1991, 81-84. (b) Ma, D.; Yang, J. J. Am. Chem. Soc. 2001, 123, 9706-9707. Other workers have also reported levels of selectivity similar to our own. See: (c) Chiesa, M. V.; Manzoni, L.; Scalastico, C. Synlett 1996, 441-443. (d) Beal, L. M.; Moeller, K. D. Tetrahedron Lett. 1998, 39, 4639-4642. (e) Grossmith, C. E.; Senia, F.; Wagner, J. Synlett 1999, 10, 1660-1662. (f) Mulzer, J.; Schulzchen, F.; Bats, J.-W. Tetrahedron 2000, 56, 4289-4298. (g) Tong, Y.; Forbian, Y. M.; Wu, M.; Boyd, N. D.; Moeller, K. D. J. Org. Chem. 2000, 65, 2484-2493. (h) Manzoni, L.; Colombo, M.; May, E.; Scolastico, C. Tetrahedron 2001, 57, 249-255. (i) Zhang, X.; Schmitt, A. C.; Jiang, W. Tetrahedron Lett. 2001, 42, 5335-5338. (j) Kim, S.; Hayashi, K.; Kitano, Y.; Tada, M.; Chiba, K. Org. Lett. 2002, 4, 3735-3737. (k) Harris, P. W. R.; Brimble, M. A.; Gluckman, P. D. Org. Lett. 2003, 5, 1847-1850.
18. Although this reaction has been described to furnish a 95:5 (cis:trans) ratio of diastereomers we have not been able to reproduce this result (80: 20, cis:trans obtained). See: (a) Shono, T.; Fujita, T.; Matsumura, Y. Chem. Lett. 1991, 81-84. (b) Ma, D.; Yang, J. J. Am. Chem. Soc. 2001, 123, 9706-9707. Other workers have also reported levels of selectivity similar to our own. See: (c) Chiesa, M. V.; Manzoni, L.; Scalastico, C. Synlett 1996, 441-443. (d) Beal, L. M.; Moeller, K. D. Tetrahedron Lett. 1998, 39, 4639-4642. (e) Grossmith, C. E.; Senia, F.; Wagner, J. Synlett 1999, 10, 1660-1662. (f) Mulzer, J.; Schulzchen, F.; Bats, J.-W. Tetrahedron 2000, 56, 4289-4298. (g) Tong, Y.; Forbian, Y. M.; Wu, M.; Boyd, N. D.; Moeller, K. D. J. Org. Chem. 2000, 65, 2484-2493. (h) Manzoni, L.; Colombo, M.; May, E.; Scolastico, C. Tetrahedron 2001, 57, 249-255. (i) Zhang, X.; Schmitt, A. C.; Jiang, W. Tetrahedron Lett. 2001, 42, 5335-5338. (j) Kim, S.; Hayashi, K.; Kitano, Y.; Tada, M.; Chiba, K. Org. Lett. 2002, 4, 3735-3737. (k) Harris, P. W. R.; Brimble, M. A.; Gluckman, P. D. Org. Lett. 2003, 5, 1847-1850.
19. Although this reaction has been described to furnish a 95:5 (cis:trans) ratio of diastereomers we have not been able to reproduce this result (80: 20, cis:trans obtained). See: (a) Shono, T.; Fujita, T.; Matsumura, Y. Chem. Lett. 1991, 81-84. (b) Ma, D.; Yang, J. J. Am. Chem. Soc. 2001, 123, 9706-9707. Other workers have also reported levels of selectivity similar to our own. See: (c) Chiesa, M. V.; Manzoni, L.; Scalastico, C. Synlett 1996, 441-443. (d) Beal, L. M.; Moeller, K. D. Tetrahedron Lett. 1998, 39, 4639-4642. (e) Grossmith, C. E.; Senia, F.; Wagner, J. Synlett 1999, 10, 1660-1662. (f) Mulzer, J.; Schulzchen, F.; Bats, J.-W. Tetrahedron 2000, 56, 4289-4298. (g) Tong, Y.; Forbian, Y. M.; Wu, M.; Boyd, N. D.; Moeller, K. D. J. Org. Chem. 2000, 65, 2484-2493. (h) Manzoni, L.; Colombo, M.; May, E.; Scolastico, C. Tetrahedron 2001, 57, 249-255. (i) Zhang, X.; Schmitt, A. C.; Jiang, W. Tetrahedron Lett. 2001, 42, 5335-5338. (j) Kim, S.; Hayashi, K.; Kitano, Y.; Tada, M.; Chiba, K. Org. Lett. 2002, 4, 3735-3737. (k) Harris, P. W. R.; Brimble, M. A.; Gluckman, P. D. Org. Lett. 2003, 5, 1847-1850.
20. Although this reaction has been described to furnish a 95:5 (cis:trans) ratio of diastereomers we have not been able to reproduce this result (80: 20, cis:trans obtained). See: (a) Shono, T.; Fujita, T.; Matsumura, Y. Chem. Lett. 1991, 81-84. (b) Ma, D.; Yang, J. J. Am. Chem. Soc. 2001, 123, 9706-9707. Other workers have also reported levels of selectivity similar to our own. See: (c) Chiesa, M. V.; Manzoni, L.; Scalastico, C. Synlett 1996, 441-443. (d) Beal, L. M.; Moeller, K. D. Tetrahedron Lett. 1998, 39, 4639-4642. (e) Grossmith, C. E.; Senia, F.; Wagner, J. Synlett 1999, 10, 1660-1662. (f) Mulzer, J.; Schulzchen, F.; Bats, J.-W. Tetrahedron 2000, 56, 4289-4298. (g) Tong, Y.; Forbian, Y. M.; Wu, M.; Boyd, N. D.; Moeller, K. D. J. Org. Chem. 2000, 65, 2484-2493. (h) Manzoni, L.; Colombo, M.; May, E.; Scolastico, C. Tetrahedron 2001, 57, 249-255. (i) Zhang, X.; Schmitt, A. C.; Jiang, W. Tetrahedron Lett. 2001, 42, 5335-5338. (j) Kim, S.; Hayashi, K.; Kitano, Y.; Tada, M.; Chiba, K. Org. Lett. 2002, 4, 3735-3737. (k) Harris, P. W. R.; Brimble, M. A.; Gluckman, P. D. Org. Lett. 2003, 5, 1847-1850.
21. Although this reaction has been described to furnish a 95:5 (cis:trans) ratio of diastereomers we have not been able to reproduce this result (80: 20, cis:trans obtained). See: (a) Shono, T.; Fujita, T.; Matsumura, Y. Chem. Lett. 1991, 81-84. (b) Ma, D.; Yang, J. J. Am. Chem. Soc. 2001, 123, 9706-9707. Other workers have also reported levels of selectivity similar to our own. See: (c) Chiesa, M. V.; Manzoni, L.; Scalastico, C. Synlett 1996, 441-443. (d) Beal, L. M.; Moeller, K. D. Tetrahedron Lett. 1998, 39, 4639-4642. (e) Grossmith, C. E.; Senia, F.; Wagner, J. Synlett 1999, 10, 1660-1662. (f) Mulzer, J.; Schulzchen, F.; Bats, J.-W. Tetrahedron 2000, 56, 4289-4298. (g) Tong, Y.; Forbian, Y. M.; Wu, M.; Boyd, N. D.; Moeller, K. D. J. Org. Chem. 2000, 65, 2484-2493. (h) Manzoni, L.; Colombo, M.; May, E.; Scolastico, C. Tetrahedron 2001, 57, 249-255. (i) Zhang, X.; Schmitt, A. C.; Jiang, W. Tetrahedron Lett. 2001, 42, 5335-5338. (j) Kim, S.; Hayashi, K.; Kitano, Y.; Tada, M.; Chiba, K. Org. Lett. 2002, 4, 3735-3737. (k) Harris, P. W. R.; Brimble, M. A.; Gluckman, P. D. Org. Lett. 2003, 5, 1847-1850.
22. Although this reaction has been described to furnish a 95:5 (cis:trans) ratio of diastereomers we have not been able to reproduce this result (80: 20, cis:trans obtained). See: (a) Shono, T.; Fujita, T.; Matsumura, Y. Chem. Lett. 1991, 81-84. (b) Ma, D.; Yang, J. J. Am. Chem. Soc. 2001, 123, 9706-9707. Other workers have also reported levels of selectivity similar to our own. See: (c) Chiesa, M. V.; Manzoni, L.; Scalastico, C. Synlett 1996, 441-443. (d) Beal, L. M.; Moeller, K. D. Tetrahedron Lett. 1998, 39, 4639-4642. (e) Grossmith, C. E.; Senia, F.; Wagner, J. Synlett 1999, 10, 1660-1662. (f) Mulzer, J.; Schulzchen, F.; Bats, J.-W. Tetrahedron 2000, 56, 4289-4298. (g) Tong, Y.; Forbian, Y. M.; Wu, M.; Boyd, N. D.; Moeller, K. D. J. Org. Chem. 2000, 65, 2484-2493. (h) Manzoni, L.; Colombo, M.; May, E.; Scolastico, C. Tetrahedron 2001, 57, 249-255. (i) Zhang, X.; Schmitt, A. C.; Jiang, W. Tetrahedron Lett. 2001, 42, 5335-5338. (j) Kim, S.; Hayashi, K.; Kitano, Y.; Tada, M.; Chiba, K. Org. Lett. 2002, 4, 3735-3737. (k) Harris, P. W. R.; Brimble, M. A.; Gluckman, P. D. Org. Lett. 2003, 5, 1847-1850.
23. Although this reaction has been described to furnish a 95:5 (cis:trans) ratio of diastereomers we have not been able to reproduce this result (80: 20, cis:trans obtained). See: (a) Shono, T.; Fujita, T.; Matsumura, Y. Chem. Lett. 1991, 81-84. (b) Ma, D.; Yang, J. J. Am. Chem. Soc. 2001, 123, 9706-9707. Other workers have also reported levels of selectivity similar to our own. See: (c) Chiesa, M. V.; Manzoni, L.; Scalastico, C. Synlett 1996, 441-443. (d) Beal, L. M.; Moeller, K. D. Tetrahedron Lett. 1998, 39, 4639-4642. (e) Grossmith, C. E.; Senia, F.; Wagner, J. Synlett 1999, 10, 1660-1662. (f) Mulzer, J.; Schulzchen, F.; Bats, J.-W. Tetrahedron 2000, 56, 4289-4298. (g) Tong, Y.; Forbian, Y. M.; Wu, M.; Boyd, N. D.; Moeller, K. D. J. Org. Chem. 2000, 65, 2484-2493. (h) Manzoni, L.; Colombo, M.; May, E.; Scolastico, C. Tetrahedron 2001, 57, 249-255. (i) Zhang, X.; Schmitt, A. C.; Jiang, W. Tetrahedron Lett. 2001, 42, 5335-5338. (j) Kim, S.; Hayashi, K.; Kitano, Y.; Tada, M.; Chiba, K. Org. Lett. 2002, 4, 3735-3737. (k) Harris, P. W. R.; Brimble, M. A.; Gluckman, P. D. Org. Lett. 2003, 5, 1847-1850.
24. Although this reaction has been described to furnish a 95:5 (cis:trans) ratio of diastereomers we have not been able to reproduce this result (80: 20, cis:trans obtained). See: (a) Shono, T.; Fujita, T.; Matsumura, Y. Chem. Lett. 1991, 81-84. (b) Ma, D.; Yang, J. J. Am. Chem. Soc. 2001, 123, 9706-9707. Other workers have also reported levels of selectivity similar to our own. See: (c) Chiesa, M. V.; Manzoni, L.; Scalastico, C. Synlett 1996, 441-443. (d) Beal, L. M.; Moeller, K. D. Tetrahedron Lett. 1998, 39, 4639-4642. (e) Grossmith, C. E.; Senia, F.; Wagner, J. Synlett 1999, 10, 1660-1662. (f) Mulzer, J.; Schulzchen, F.; Bats, J.-W. Tetrahedron 2000, 56, 4289-4298. (g) Tong, Y.; Forbian, Y. M.; Wu, M.; Boyd, N. D.; Moeller, K. D. J. Org. Chem. 2000, 65, 2484-2493. (h) Manzoni, L.; Colombo, M.; May, E.; Scolastico, C. Tetrahedron 2001, 57, 249-255. (i) Zhang, X.; Schmitt, A. C.; Jiang, W. Tetrahedron Lett. 2001, 42, 5335-5338. (j) Kim, S.; Hayashi, K.; Kitano, Y.; Tada, M.; Chiba, K. Org. Lett. 2002, 4, 3735-3737. (k) Harris, P. W. R.; Brimble, M. A.; Gluckman, P. D. Org. Lett. 2003, 5, 1847-1850.
25. Although this reaction has been described to furnish a 95:5 (cis:trans) ratio of diastereomers we have not been able to reproduce this result (80: 20, cis:trans obtained). See: (a) Shono, T.; Fujita, T.; Matsumura, Y. Chem. Lett. 1991, 81-84. (b) Ma, D.; Yang, J. J. Am. Chem. Soc. 2001, 123, 9706-9707. Other workers have also reported levels of selectivity similar to our own. See: (c) Chiesa, M. V.; Manzoni, L.; Scalastico, C. Synlett 1996, 441-443. (d) Beal, L. M.; Moeller, K. D. Tetrahedron Lett. 1998, 39, 4639-4642. (e) Grossmith, C. E.; Senia, F.; Wagner, J. Synlett 1999, 10, 1660-1662. (f) Mulzer, J.; Schulzchen, F.; Bats, J.-W. Tetrahedron 2000, 56, 4289-4298. (g) Tong, Y.; Forbian, Y. M.; Wu, M.; Boyd, N. D.; Moeller, K. D. J. Org. Chem. 2000, 65, 2484-2493. (h) Manzoni, L.; Colombo, M.; May, E.; Scolastico, C. Tetrahedron 2001, 57, 249-255. (i) Zhang, X.; Schmitt, A. C.; Jiang, W. Tetrahedron Lett. 2001, 42, 5335-5338. (j) Kim, S.; Hayashi, K.; Kitano, Y.; Tada, M.; Chiba, K. Org. Lett. 2002, 4, 3735-3737. (k) Harris, P. W. R.; Brimble, M. A.; Gluckman, P. D. Org. Lett. 2003, 5, 1847-1850.
26. Takai, K.; Kataoka, Y.; Miyai, J.; Okazoe, T.; Oshima, K.; Utimoto, K. Org. Synth. 1996, 73, 73-84.
27. Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039-2041.
28. Scholl, M.; Ding, S.; Lee. C. W.; Grubbs. R. H. Org. Lett. 1999, 1, 953-956.
29. Love, J. A.; Morgan, J. P.; Trnka, T. M.; Grubbs, R. H. Angew. Chem., Int. Ed. 2002, 41, 4035-4037.
30. Murdzek, J. S.; Schrock, R. R. Organometallics 1987, 6, 1373-1374.
31. Grubbs 1st, 2nd, and 3rd generation catalysts in either dichloromethane or benzene, Schrocks catalyst in degassed pentane, at both room temperature and reflux, with concentrations ranging from 0.005 to 0.1 M.
32. (a) Louie, J.; Grubbs, R. H. Organometallics 2002, 21, 2153-2164 and references therein.
33. (b) Aggarwal, V. K.; Daly, A. D. Chem. Commun. 2002, 2490-2491.
34. (a) Rodríguez, J. R.; Castedo, L.; Mascareñas. J. L. Chem. Eur. J. 2002, 8, 2923-2930.
35. (b) Neipp, C. E.; Martin, S. F. J. Org. Chem. 2003, 68, 8867-8878 and references therein.
36. (a) Gilbert, J. C.; Weerasooriya, U. J. Org. Chem. 1982, 47, 1837-1845.
37. (b) Ohira, S. Synth. Commun. 1989, 19, 561-564.
38. (c) Müller, S.; Liepold, B.; Roth, G. J.; Bestmann, H. J. Synlett 1996, 521-522.
39. Mori, M.; Sakakibara, N.; Kinoshita, A. J. Org. Chem. 1998, 63, 3, 6082-6083. For a review of enyne metathesis see ref 3h.
40. GC-MS analysis of the reaction mixture only showed product and starting material, implying that the byproducts formed are nonvolatile. We speculate that the active metathesis catalyst was converting the desired product 15 into the (nonvolatile) homodimer.
41. For recent examples, see: (a) Fürstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H.-J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204-2207. (b) Boiteau, J.; Van de Weghe, P.; Eustache, J. Org. Lett. 2001, 3, 2737-2740. (c) Fürstner, A.; Guth, O.; Düffels, A.; Seidel, G.; Liebl, M.; Gabor, B.; Mynott, R. Chem. Eur. J. 2001, 7, 4811-4820. (d) Clark, J. S.; Elustondo, F.; Trevitt, G. P.; Boyall, D.; Robertson, J.; Blake, A. J.; Wilson, C.; Stammen, B. Tetrahedron 2002, 58, 1973-1982. (e) Poulsen, C. S.; Madsen, R. J. Org. Chem. 2002, 67, 4441-4449.
42. For recent examples, see: (a) Fürstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H.-J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204-2207. (b) Boiteau, J.; Van de Weghe, P.; Eustache, J. Org. Lett. 2001, 3, 2737-2740. (c) Fürstner, A.; Guth, O.; Düffels, A.; Seidel, G.; Liebl, M.; Gabor, B.; Mynott, R. Chem. Eur. J. 2001, 7, 4811-4820. (d) Clark, J. S.; Elustondo, F.; Trevitt, G. P.; Boyall, D.; Robertson, J.; Blake, A. J.; Wilson, C.; Stammen, B. Tetrahedron 2002, 58, 1973-1982. (e) Poulsen, C. S.; Madsen, R. J. Org. Chem. 2002, 67, 4441-4449.
43. For recent examples, see: (a) Fürstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H.-J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204-2207. (b) Boiteau, J.; Van de Weghe, P.; Eustache, J. Org. Lett. 2001, 3, 2737-2740. (c) Fürstner, A.; Guth, O.; Düffels, A.; Seidel, G.; Liebl, M.; Gabor, B.; Mynott, R. Chem. Eur. J. 2001, 7, 4811-4820. (d) Clark, J. S.; Elustondo, F.; Trevitt, G. P.; Boyall, D.; Robertson, J.; Blake, A. J.; Wilson, C.; Stammen, B. Tetrahedron 2002, 58, 1973-1982. (e) Poulsen, C. S.; Madsen, R. J. Org. Chem. 2002, 67, 4441-4449.
44. For recent examples, see: (a) Fürstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H.-J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204-2207. (b) Boiteau, J.; Van de Weghe, P.; Eustache, J. Org. Lett. 2001, 3, 2737-2740. (c) Fürstner, A.; Guth, O.; Düffels, A.; Seidel, G.; Liebl, M.; Gabor, B.; Mynott, R. Chem. Eur. J. 2001, 7, 4811-4820. (d) Clark, J. S.; Elustondo, F.; Trevitt, G. P.; Boyall, D.; Robertson, J.; Blake, A. J.; Wilson, C.; Stammen, B. Tetrahedron 2002, 58, 1973-1982. (e) Poulsen, C. S.; Madsen, R. J. Org. Chem. 2002, 67, 4441-4449.
45. For recent examples, see: (a) Fürstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H.-J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204-2207. (b) Boiteau, J.; Van de Weghe, P.; Eustache, J. Org. Lett. 2001, 3, 2737-2740. (c) Fürstner, A.; Guth, O.; Düffels, A.; Seidel, G.; Liebl, M.; Gabor, B.; Mynott, R. Chem. Eur. J. 2001, 7, 4811-4820. (d) Clark, J. S.; Elustondo, F.; Trevitt, G. P.; Boyall, D.; Robertson, J.; Blake, A. J.; Wilson, C.; Stammen, B. Tetrahedron 2002, 58, 1973-1982. (e) Poulsen, C. S.; Madsen, R. J. Org. Chem. 2002, 67, 4441-4449.
46. Hernandez, A. S.; Thaler, A.; Castells, J.; Rapoport, H. J. Org. Chem. 1996, 61, 314-323.
47. For one of the best previous syntheses of ferruginine (8 steps, 11% overall yield), see: Gauthier, I.; Royer, J.; Husson, H.-P. J. Org. Chem. 1997, 62, 6704-6705.