Ready Access to Bicyclo[5.3.0]decan-1-ones and to Bicyclo[6.3.0]undecan-1-ones by Intramolecular Pauson-Khand Reactions Using a Temporary Sulfur Bridge

Journal of Organic Chemistry

Volumn 63, Issue 10, 1998, Pages 3346-3351

  Castro, Jaume ^a   Moyano, Albert ^a   Pericàs, Miquel A ^a   Riera, Antoni ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001758174     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9722257     Document Type: Article

References (62)

1. For general references on the synthesis of natural products with perhydroazulene and perhydrocyclopentanecyclooctene skeletons, see: (a) ApSimon, J.; Ed. The Total Synthesis of Natural Products; Wiley-Interscience: New York, 1973-1992; Vols. 1-9. (b) Ho, TseLok. Carbocycle Construction in Terpene Synthesis; VCH Publishers: Weinheim, 1988. (c) Rigby, J. H. In Studies in Natural Products Chemistry; Rahman, A., Ed.; Elsevier: New York, 1988; Vol. 1, pp 545-576. (d) Corey, E. J.; Cheng, X.-M. The Logic of Chemical Synthesis; John Wiley & Sons: New York, 1989.
2. For general references on the synthesis of natural products with perhydroazulene and perhydrocyclopentanecyclooctene skeletons, see: (a) ApSimon, J.; Ed. The Total Synthesis of Natural Products; Wiley-Interscience: New York, 1973-1992; Vols. 1-9. (b) Ho, TseLok. Carbocycle Construction in Terpene Synthesis; VCH Publishers: Weinheim, 1988. (c) Rigby, J. H. In Studies in Natural Products Chemistry; Rahman, A., Ed.; Elsevier: New York, 1988; Vol. 1, pp 545-576. (d) Corey, E. J.; Cheng, X.-M. The Logic of Chemical Synthesis; John Wiley & Sons: New York, 1989.
3. For general references on the synthesis of natural products with perhydroazulene and perhydrocyclopentanecyclooctene skeletons, see: (a) ApSimon, J.; Ed. The Total Synthesis of Natural Products; Wiley-Interscience: New York, 1973-1992; Vols. 1-9. (b) Ho, TseLok. Carbocycle Construction in Terpene Synthesis; VCH Publishers: Weinheim, 1988. (c) Rigby, J. H. In Studies in Natural Products Chemistry; Rahman, A., Ed.; Elsevier: New York, 1988; Vol. 1, pp 545-576. (d) Corey, E. J.; Cheng, X.-M. The Logic of Chemical Synthesis; John Wiley & Sons: New York, 1989.
4. For general references on the synthesis of natural products with perhydroazulene and perhydrocyclopentanecyclooctene skeletons, see: (a) ApSimon, J.; Ed. The Total Synthesis of Natural Products; Wiley-Interscience: New York, 1973-1992; Vols. 1-9. (b) Ho, TseLok. Carbocycle Construction in Terpene Synthesis; VCH Publishers: Weinheim, 1988. (c) Rigby, J. H. In Studies in Natural Products Chemistry; Rahman, A., Ed.; Elsevier: New York, 1988; Vol. 1, pp 545-576. (d) Corey, E. J.; Cheng, X.-M. The Logic of Chemical Synthesis; John Wiley & Sons: New York, 1989.
5. For reviews on cyclopentaannulation reactions, see: (a) Trost, B. M. Chem. Soc. Rev. 1982, 11, 141-170. (b) Ramaiah, M. Synthesis 1984, 529-560. (c) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer-Verlag: Berlin, 1987. (d) Hudlicky, T.; Price, J. Chem. Rev. 1989, 89, 1467-1486.
6. For reviews on cyclopentaannulation reactions, see: (a) Trost, B. M. Chem. Soc. Rev. 1982, 11, 141-170. (b) Ramaiah, M. Synthesis 1984, 529-560. (c) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer-Verlag: Berlin, 1987. (d) Hudlicky, T.; Price, J. Chem. Rev. 1989, 89, 1467-1486.
7. For reviews on cyclopentaannulation reactions, see: (a) Trost, B. M. Chem. Soc. Rev. 1982, 11, 141-170. (b) Ramaiah, M. Synthesis 1984, 529-560. (c) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer-Verlag: Berlin, 1987. (d) Hudlicky, T.; Price, J. Chem. Rev. 1989, 89, 1467-1486.
8. For reviews on cyclopentaannulation reactions, see: (a) Trost, B. M. Chem. Soc. Rev. 1982, 11, 141-170. (b) Ramaiah, M. Synthesis 1984, 529-560. (c) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer-Verlag: Berlin, 1987. (d) Hudlicky, T.; Price, J. Chem. Rev. 1989, 89, 1467-1486.
9. Ni: (a) Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4679. (b) Wender, P. A.; Ihle, N. C.; Correia, C. R. D. J. Am. Chem. Soc. 1988, 110, 5904-5906. (c) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (d) Pagès, LI.; Llebaria, A., Camps, F.; Molins, E.; Miravitlles, C.; Moretó, J. M. J. Am. Chem. Soc. 1992, 114, 10449-10461.
10. Ni: (a) Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4679. (b) Wender, P. A.; Ihle, N. C.; Correia, C. R. D. J. Am. Chem. Soc. 1988, 110, 5904-5906. (c) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (d) Pagès, LI.; Llebaria, A., Camps, F.; Molins, E.; Miravitlles, C.; Moretó, J. M. J. Am. Chem. Soc. 1992, 114, 10449-10461.
11. Ni: (a) Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4679. (b) Wender, P. A.; Ihle, N. C.; Correia, C. R. D. J. Am. Chem. Soc. 1988, 110, 5904-5906. (c) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (d) Pagès, LI.; Llebaria, A., Camps, F.; Molins, E.; Miravitlles, C.; Moretó, J. M. J. Am. Chem. Soc. 1992, 114, 10449-10461.
12. Ni: (a) Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4679. (b) Wender, P. A.; Ihle, N. C.; Correia, C. R. D. J. Am. Chem. Soc. 1988, 110, 5904-5906. (c) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (d) Pagès, LI.; Llebaria, A., Camps, F.; Molins, E.; Miravitlles, C.; Moretó, J. M. J. Am. Chem. Soc. 1992, 114, 10449-10461.
13. Rh: (a) Dauben, W. G.; Dinges, J.; Smith, T. C. J. Org. Chem. 1993, 58, 7635-7367. (b) McMills, M. C.; Zhuang, L.; Wright, D. L.; Wat, W. Tetrahedron Lett. 1994, 35, 8311-8314. (c) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem, Soc. 1995, 117, 4720-4721. Co: (d) Lautens, M.; Tam, W.; Lautens, J. C.; Edwards, L. G.; Grudden, C. M.; Smith, A. C. J. Am. Chem. Soc. 1995, 117, 6863-6879. (e) Renaud, J.-L.; Petit, M.; Aubert, C.; Malacria, M. Synlett 1997, 931-932.
14. Rh: (a) Dauben, W. G.; Dinges, J.; Smith, T. C. J. Org. Chem. 1993, 58, 7635-7367. (b) McMills, M. C.; Zhuang, L.; Wright, D. L.; Wat, W. Tetrahedron Lett. 1994, 35, 8311-8314. (c) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem, Soc. 1995, 117, 4720-4721. Co: (d) Lautens, M.; Tam, W.; Lautens, J. C.; Edwards, L. G.; Grudden, C. M.; Smith, A. C. J. Am. Chem. Soc. 1995, 117, 6863-6879. (e) Renaud, J.-L.; Petit, M.; Aubert, C.; Malacria, M. Synlett 1997, 931-932.
15. Rh: (a) Dauben, W. G.; Dinges, J.; Smith, T. C. J. Org. Chem. 1993, 58, 7635-7367. (b) McMills, M. C.; Zhuang, L.; Wright, D. L.; Wat, W. Tetrahedron Lett. 1994, 35, 8311-8314. (c) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem, Soc. 1995, 117, 4720-4721. Co: (d) Lautens, M.; Tam, W.; Lautens, J. C.; Edwards, L. G.; Grudden, C. M.; Smith, A. C. J. Am. Chem. Soc. 1995, 117, 6863-6879. (e) Renaud, J.-L.; Petit, M.; Aubert, C.; Malacria, M. Synlett 1997, 931-932.
16. Rh: (a) Dauben, W. G.; Dinges, J.; Smith, T. C. J. Org. Chem. 1993, 58, 7635-7367. (b) McMills, M. C.; Zhuang, L.; Wright, D. L.; Wat, W. Tetrahedron Lett. 1994, 35, 8311-8314. (c) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem, Soc. 1995, 117, 4720-4721. Co: (d) Lautens, M.; Tam, W.; Lautens, J. C.; Edwards, L. G.; Grudden, C. M.; Smith, A. C. J. Am. Chem. Soc. 1995, 117, 6863-6879. (e) Renaud, J.-L.; Petit, M.; Aubert, C.; Malacria, M. Synlett 1997, 931-932.
17. Rh: (a) Dauben, W. G.; Dinges, J.; Smith, T. C. J. Org. Chem. 1993, 58, 7635-7367. (b) McMills, M. C.; Zhuang, L.; Wright, D. L.; Wat, W. Tetrahedron Lett. 1994, 35, 8311-8314. (c) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem, Soc. 1995, 117, 4720-4721. Co: (d) Lautens, M.; Tam, W.; Lautens, J. C.; Edwards, L. G.; Grudden, C. M.; Smith, A. C. J. Am. Chem. Soc. 1995, 117, 6863-6879. (e) Renaud, J.-L.; Petit, M.; Aubert, C.; Malacria, M. Synlett 1997, 931-932.
18. Pd: (a) Trost, B. M.; Nanninga, T. N.; Chan, D. M. T. Organometallics 1982, 1, 1543-1545. (b) Trost, B. M.; McPherson, D. T. J. Am. Chem. Soc. 1987, 109, 3483-3484. (c) Trost, B. M.; Greese, T. J. Am. Chem. Soc. 1991, 113, 7363-7372.
19. Pd: (a) Trost, B. M.; Nanninga, T. N.; Chan, D. M. T. Organometallics 1982, 1, 1543-1545. (b) Trost, B. M.; McPherson, D. T. J. Am. Chem. Soc. 1987, 109, 3483-3484. (c) Trost, B. M.; Greese, T. J. Am. Chem. Soc. 1991, 113, 7363-7372.
20. Pd: (a) Trost, B. M.; Nanninga, T. N.; Chan, D. M. T. Organometallics 1982, 1, 1543-1545. (b) Trost, B. M.; McPherson, D. T. J. Am. Chem. Soc. 1987, 109, 3483-3484. (c) Trost, B. M.; Greese, T. J. Am. Chem. Soc. 1991, 113, 7363-7372.
21. Zr: (a) Negishi, E.; Ma, S.; Sugihara, T.; Noda, Y. J. Org. Chem. 1997, 62, 1922-1923. (b) Wender, P. A.; McDonald, F. Tetrahedron Lett. 1990, 31, 3691-3694. (c) Wender, P. A.; Rice, K. D.; Schnute, M. E. J. Am. Chem. Soc. 1997, 119, 7897-7898.
22. Zr: (a) Negishi, E.; Ma, S.; Sugihara, T.; Noda, Y. J. Org. Chem. 1997, 62, 1922-1923. (b) Wender, P. A.; McDonald, F. Tetrahedron Lett. 1990, 31, 3691-3694. (c) Wender, P. A.; Rice, K. D.; Schnute, M. E. J. Am. Chem. Soc. 1997, 119, 7897-7898.
23. Zr: (a) Negishi, E.; Ma, S.; Sugihara, T.; Noda, Y. J. Org. Chem. 1997, 62, 1922-1923. (b) Wender, P. A.; McDonald, F. Tetrahedron Lett. 1990, 31, 3691-3694. (c) Wender, P. A.; Rice, K. D.; Schnute, M. E. J. Am. Chem. Soc. 1997, 119, 7897-7898.
24. Fe: (a) Booker-Millburn, K. I.; Thompson, D. F. Synlett 1993, 592-594.
25. Ru: (b) Kim, S.-M.; Zuercker, W. J.; Dowden, W. B.; Grubbs, R. H. J. Org. Chem. 1996, 61, 1073-1081. (c) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746-8749. (d) Ishii, S.; Helquist, P. Synlett 1997, 508-510.
26. Ru: (b) Kim, S.-M.; Zuercker, W. J.; Dowden, W. B.; Grubbs, R. H. J. Org. Chem. 1996, 61, 1073-1081. (c) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746-8749. (d) Ishii, S.; Helquist, P. Synlett 1997, 508-510.
27. Ru: (b) Kim, S.-M.; Zuercker, W. J.; Dowden, W. B.; Grubbs, R. H. J. Org. Chem. 1996, 61, 1073-1081. (c) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746-8749. (d) Ishii, S.; Helquist, P. Synlett 1997, 508-510.
28. Mn: Iwasawa, N.; Funahashi, M.; Narasaka, K. Chem. Lett. 1994, 1697-1700.
29. Reviews on the Pauson-Khand reaction: (a) Pauson, P. L.; Khand, I. U. Ann, N. Y. Acad. Sci. 1977, 295, 2-14. (b) Pauson, P. L. Tetrahedron 1986, 41, 5855-5860. (c) Pauson, P. L. In Organometallics in Organic Synthesis. Aspects of a Modern Interdisciplinary Field; de Meijere, A., tom Dieck, H., Eds.; Springer: Berlin, 1988; pp 233-246. (d) Harrington, P. J. Transition Metals in Total Synthesis; Wiley: New York, 1990; pp 259-301. (e) Schore, N. E. Org. React. 1991, 40, 1-90. (f) Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 1037-1064.
30. Reviews on the Pauson-Khand reaction: (a) Pauson, P. L.; Khand, I. U. Ann, N. Y. Acad. Sci. 1977, 295, 2-14. (b) Pauson, P. L. Tetrahedron 1986, 41, 5855-5860. (c) Pauson, P. L. In Organometallics in Organic Synthesis. Aspects of a Modern Interdisciplinary Field; de Meijere, A., tom Dieck, H., Eds.; Springer: Berlin, 1988; pp 233-246. (d) Harrington, P. J. Transition Metals in Total Synthesis; Wiley: New York, 1990; pp 259-301. (e) Schore, N. E. Org. React. 1991, 40, 1-90. (f) Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 1037-1064.
31. Reviews on the Pauson-Khand reaction: (a) Pauson, P. L.; Khand, I. U. Ann, N. Y. Acad. Sci. 1977, 295, 2-14. (b) Pauson, P. L. Tetrahedron 1986, 41, 5855-5860. (c) Pauson, P. L. In Organometallics in Organic Synthesis. Aspects of a Modern Interdisciplinary Field; de Meijere, A., tom Dieck, H., Eds.; Springer: Berlin, 1988; pp 233-246. (d) Harrington, P. J. Transition Metals in Total Synthesis; Wiley: New York, 1990; pp 259-301. (e) Schore, N. E. Org. React. 1991, 40, 1-90. (f) Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 1037-1064.
32. Reviews on the Pauson-Khand reaction: (a) Pauson, P. L.; Khand, I. U. Ann, N. Y. Acad. Sci. 1977, 295, 2-14. (b) Pauson, P. L. Tetrahedron 1986, 41, 5855-5860. (c) Pauson, P. L. In Organometallics in Organic Synthesis. Aspects of a Modern Interdisciplinary Field; de Meijere, A., tom Dieck, H., Eds.; Springer: Berlin, 1988; pp 233-246. (d) Harrington, P. J. Transition Metals in Total Synthesis; Wiley: New York, 1990; pp 259-301. (e) Schore, N. E. Org. React. 1991, 40, 1-90. (f) Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 1037-1064.
33. Reviews on the Pauson-Khand reaction: (a) Pauson, P. L.; Khand, I. U. Ann, N. Y. Acad. Sci. 1977, 295, 2-14. (b) Pauson, P. L. Tetrahedron 1986, 41, 5855-5860. (c) Pauson, P. L. In Organometallics in Organic Synthesis. Aspects of a Modern Interdisciplinary Field; de Meijere, A., tom Dieck, H., Eds.; Springer: Berlin, 1988; pp 233-246. (d) Harrington, P. J. Transition Metals in Total Synthesis; Wiley: New York, 1990; pp 259-301. (e) Schore, N. E. Org. React. 1991, 40, 1-90. (f) Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 1037-1064.
34. Reviews on the Pauson-Khand reaction: (a) Pauson, P. L.; Khand, I. U. Ann, N. Y. Acad. Sci. 1977, 295, 2-14. (b) Pauson, P. L. Tetrahedron 1986, 41, 5855-5860. (c) Pauson, P. L. In Organometallics in Organic Synthesis. Aspects of a Modern Interdisciplinary Field; de Meijere, A., tom Dieck, H., Eds.; Springer: Berlin, 1988; pp 233-246. (d) Harrington, P. J. Transition Metals in Total Synthesis; Wiley: New York, 1990; pp 259-301. (e) Schore, N. E. Org. React. 1991, 40, 1-90. (f) Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 1037-1064.
35. For some recent leading references, see: (a) Magnus, P.; Slater, M. J.; Principe, L. M. J. Org. Chem. 1989, 54, 5148-5153. (b) Price, M. E.; Schore, N. E. J. Org. Chem. 1989, 54, 5662-5667. (c) Dauben, W. G.; Kowalczyk, B. A. Tetrahedron Lett. 1990, 31, 635-638. (d) Rowley, E. G.; Schore, N. E. J. Org. Chem. 1992, 57, 6853-6861. (e) Krafft, M. E.; Wright, C. Tetrahedron Lett. 1992, 33, 151-152. (f) Krafft, M. E.; Chirico, C. Tetrahedron Lett. 1994, 35, 4511-4514. (g) Veretenov, A. L.; Koltun, D. O.; Smit, W. A.; Strelenko, Y. A. Tetrahedron Lett. 1995, 36, 4651-4654. (h) Paquette, L. A.; Borrelly, S. J. Org. Chem. 1995, 60, 6912-6921.
36. For some recent leading references, see: (a) Magnus, P.; Slater, M. J.; Principe, L. M. J. Org. Chem. 1989, 54, 5148-5153. (b) Price, M. E.; Schore, N. E. J. Org. Chem. 1989, 54, 5662-5667. (c) Dauben, W. G.; Kowalczyk, B. A. Tetrahedron Lett. 1990, 31, 635-638. (d) Rowley, E. G.; Schore, N. E. J. Org. Chem. 1992, 57, 6853-6861. (e) Krafft, M. E.; Wright, C. Tetrahedron Lett. 1992, 33, 151-152. (f) Krafft, M. E.; Chirico, C. Tetrahedron Lett. 1994, 35, 4511-4514. (g) Veretenov, A. L.; Koltun, D. O.; Smit, W. A.; Strelenko, Y. A. Tetrahedron Lett. 1995, 36, 4651-4654. (h) Paquette, L. A.; Borrelly, S. J. Org. Chem. 1995, 60, 6912-6921.
37. For some recent leading references, see: (a) Magnus, P.; Slater, M. J.; Principe, L. M. J. Org. Chem. 1989, 54, 5148-5153. (b) Price, M. E.; Schore, N. E. J. Org. Chem. 1989, 54, 5662-5667. (c) Dauben, W. G.; Kowalczyk, B. A. Tetrahedron Lett. 1990, 31, 635-638. (d) Rowley, E. G.; Schore, N. E. J. Org. Chem. 1992, 57, 6853-6861. (e) Krafft, M. E.; Wright, C. Tetrahedron Lett. 1992, 33, 151-152. (f) Krafft, M. E.; Chirico, C. Tetrahedron Lett. 1994, 35, 4511-4514. (g) Veretenov, A. L.; Koltun, D. O.; Smit, W. A.; Strelenko, Y. A. Tetrahedron Lett. 1995, 36, 4651-4654. (h) Paquette, L. A.; Borrelly, S. J. Org. Chem. 1995, 60, 6912-6921.
38. For some recent leading references, see: (a) Magnus, P.; Slater, M. J.; Principe, L. M. J. Org. Chem. 1989, 54, 5148-5153. (b) Price, M. E.; Schore, N. E. J. Org. Chem. 1989, 54, 5662-5667. (c) Dauben, W. G.; Kowalczyk, B. A. Tetrahedron Lett. 1990, 31, 635-638. (d) Rowley, E. G.; Schore, N. E. J. Org. Chem. 1992, 57, 6853-6861. (e) Krafft, M. E.; Wright, C. Tetrahedron Lett. 1992, 33, 151-152. (f) Krafft, M. E.; Chirico, C. Tetrahedron Lett. 1994, 35, 4511-4514. (g) Veretenov, A. L.; Koltun, D. O.; Smit, W. A.; Strelenko, Y. A. Tetrahedron Lett. 1995, 36, 4651-4654. (h) Paquette, L. A.; Borrelly, S. J. Org. Chem. 1995, 60, 6912-6921.
39. For some recent leading references, see: (a) Magnus, P.; Slater, M. J.; Principe, L. M. J. Org. Chem. 1989, 54, 5148-5153. (b) Price, M. E.; Schore, N. E. J. Org. Chem. 1989, 54, 5662-5667. (c) Dauben, W. G.; Kowalczyk, B. A. Tetrahedron Lett. 1990, 31, 635-638. (d) Rowley, E. G.; Schore, N. E. J. Org. Chem. 1992, 57, 6853-6861. (e) Krafft, M. E.; Wright, C. Tetrahedron Lett. 1992, 33, 151-152. (f) Krafft, M. E.; Chirico, C. Tetrahedron Lett. 1994, 35, 4511-4514. (g) Veretenov, A. L.; Koltun, D. O.; Smit, W. A.; Strelenko, Y. A. Tetrahedron Lett. 1995, 36, 4651-4654. (h) Paquette, L. A.; Borrelly, S. J. Org. Chem. 1995, 60, 6912-6921.
40. For some recent leading references, see: (a) Magnus, P.; Slater, M. J.; Principe, L. M. J. Org. Chem. 1989, 54, 5148-5153. (b) Price, M. E.; Schore, N. E. J. Org. Chem. 1989, 54, 5662-5667. (c) Dauben, W. G.; Kowalczyk, B. A. Tetrahedron Lett. 1990, 31, 635-638. (d) Rowley, E. G.; Schore, N. E. J. Org. Chem. 1992, 57, 6853-6861. (e) Krafft, M. E.; Wright, C. Tetrahedron Lett. 1992, 33, 151-152. (f) Krafft, M. E.; Chirico, C. Tetrahedron Lett. 1994, 35, 4511-4514. (g) Veretenov, A. L.; Koltun, D. O.; Smit, W. A.; Strelenko, Y. A. Tetrahedron Lett. 1995, 36, 4651-4654. (h) Paquette, L. A.; Borrelly, S. J. Org. Chem. 1995, 60, 6912-6921.
41. For some recent leading references, see: (a) Magnus, P.; Slater, M. J.; Principe, L. M. J. Org. Chem. 1989, 54, 5148-5153. (b) Price, M. E.; Schore, N. E. J. Org. Chem. 1989, 54, 5662-5667. (c) Dauben, W. G.; Kowalczyk, B. A. Tetrahedron Lett. 1990, 31, 635-638. (d) Rowley, E. G.; Schore, N. E. J. Org. Chem. 1992, 57, 6853-6861. (e) Krafft, M. E.; Wright, C. Tetrahedron Lett. 1992, 33, 151-152. (f) Krafft, M. E.; Chirico, C. Tetrahedron Lett. 1994, 35, 4511-4514. (g) Veretenov, A. L.; Koltun, D. O.; Smit, W. A.; Strelenko, Y. A. Tetrahedron Lett. 1995, 36, 4651-4654. (h) Paquette, L. A.; Borrelly, S. J. Org. Chem. 1995, 60, 6912-6921.
42. For some recent leading references, see: (a) Magnus, P.; Slater, M. J.; Principe, L. M. J. Org. Chem. 1989, 54, 5148-5153. (b) Price, M. E.; Schore, N. E. J. Org. Chem. 1989, 54, 5662-5667. (c) Dauben, W. G.; Kowalczyk, B. A. Tetrahedron Lett. 1990, 31, 635-638. (d) Rowley, E. G.; Schore, N. E. J. Org. Chem. 1992, 57, 6853-6861. (e) Krafft, M. E.; Wright, C. Tetrahedron Lett. 1992, 33, 151-152. (f) Krafft, M. E.; Chirico, C. Tetrahedron Lett. 1994, 35, 4511-4514. (g) Veretenov, A. L.; Koltun, D. O.; Smit, W. A.; Strelenko, Y. A. Tetrahedron Lett. 1995, 36, 4651-4654. (h) Paquette, L. A.; Borrelly, S. J. Org. Chem. 1995, 60, 6912-6921.
43. (a) Castro, J.; Sörensen, H.; Riera, A.; Morin, C.; Moyano, A.; Pericàs, M. A.; Greene, A. E. J. Am. Chem. Soc. 1990, 112, 9388-9389.
44. (b) Yoo, S.; Lee, S. H., J. Org. Chem. 1994, 59, 6968-6972.
45. Bernardes, V.; Kann, N.; Riera, A.; Moyano, A.; Pencàs, M. A.; Greene, A. E. J. Org. Chem. 1995, 60, 6670-6671.
46. Castro, J.; Moyano, A.; Pericàs, M. A.; Riera, A.; Greene, A.; Alvarez-Larena, A.; Piniella, J. F. J. Org. Chem. 1996, 67, 9016-9020.
47. (e) Donkervoort, J. G.; Gordon, A. R.; Johnstone, C.; Kerr, W. J.; Lange, U. Tetrahedron 1996, 52, 7391-7420.
48. (f) Tormo, J.; Moyano, A.; Pericàs, M. A.; Rjera, A. J. Org. Chem. 1997, 62, 4851-4856.
49. (g) Fonquerna, S.; Moyano, A.; Pencàs, M. A.; Riera, A. J. Am. Chem, Soc. 1997, 119, 10225-10226.
50. Khand, I. U.; Pauson, P. L. J. Chem. Res. (Miniprint) 1977, 0168-0187.
51. Schore and co-workers have developed an indirect approach to guaianolides and pseudoguaianolides through the intermolecular Pauson-Khand reaction of bicyclo[3.2.0]heptenes: Sampath, V., Lund, E. C.; Knudsen, M. J.; Olmstead, M. M.; Schore, N. E. J. Org. Chem. 1987, 52, 3595-3603.
52. Ahmar, M.; Locatelli, C.; Colombier, D.; Cazes, B. Tetrahedron Lett. 1997, 38, 5281-5284.
53. Jamison, T. F.; Shambayati, S.; Crowe, W. E.; Schreiber, S. L. J. Am. Chem. Soc. 1994, 116, 5505-5506.
54. The synthesis of 7-thiabicyclo[3.3.0]oct-1-en-3-ones by intramolecular Pauson-Khand reaction has also been recently reported: Stumpf, A.; Jeong, N.; Sunghee, H. Synlett 1997, 205-207.
55. Greenwood, F. L.; Kellert, M. D. J. Am. Chem. Soc. 1953, 75, 4842-4851.
56. Castro, J.; Moyano, A.; Pericàs, M. A.; Riera, A. Synthesis 1997, 518-520.
57. Jeong, N.; Chung, Y. K.; Lee, B. Y.; Lee, S. H.; Yoo, S.-E. Synlett 1991, 204-206.
58. The calculations were performed with the semiempirical MO AM1 or PM3-tm programs, as implemented in MacSpartan Plus (Wavefunction, Inc.).
59. (a) Magnus, P. C.; Exon, C.; Albaugh-Robertson, P. Tetrahedron 1985, 41, 5861-5869,
60. (b) Magnus, P. C.; Principe, L. M. Tetrahedron Lett. 1985, 26, 4851-4854.
61. Castro, J.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron 1995, 51, 6541-6556.
62. For a related example, see: Paquette, L. A.; Romine, J. L.; Lin, H.-S.; Wright, J. J. Am. Chem. Soc. 1990, 112, 9284-9292.