Rhodium-catalyzed [5 + 2] cycloadditions of allenes and vinylcyclopropanes: Asymmetric total synthesis of (+)-dictamnol

Organic Letters

Volumn 1, Issue 1, 1999, Pages 137-139

  Wender, Paul A ^a   Fuji, Masahiro ^a   Husfeld, Craig O ^a   Love, Jennifer A ^a  

^a STANFORD UNIVERSITY   (United States)

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EID: 0000678991     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990599b     Document Type: Article

References (42)

1. For representative examples, see: For [4 + 4] cycloadditions, Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4678. Wender, P. A.; Correia, C. R. D.; Ihle, N. C. J. Am. Chem. Soc. 1988, 110, 5904-5906. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. For [4 + 2] cycloadditions, 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. 1995, 60, 2962-2963. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255-1275.
2. For representative examples, see: For [4 + 4] cycloadditions, Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4678. Wender, P. A.; Correia, C. R. D.; Ihle, N. C. J. Am. Chem. Soc. 1988, 110, 5904-5906. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. For [4 + 2] cycloadditions, 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. 1995, 60, 2962-2963. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255-1275.
3. For representative examples, see: For [4 + 4] cycloadditions, Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4678. Wender, P. A.; Correia, C. R. D.; Ihle, N. C. J. Am. Chem. Soc. 1988, 110, 5904-5906. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. For [4 + 2] cycloadditions, 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. 1995, 60, 2962-2963. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255-1275.
4. For representative examples, see: For [4 + 4] cycloadditions, Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4678. Wender, P. A.; Correia, C. R. D.; Ihle, N. C. J. Am. Chem. Soc. 1988, 110, 5904-5906. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. For [4 + 2] cycloadditions, 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. 1995, 60, 2962-2963. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255-1275.
5. For representative examples, see: For [4 + 4] cycloadditions, Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4678. Wender, P. A.; Correia, C. R. D.; Ihle, N. C. J. Am. Chem. Soc. 1988, 110, 5904-5906. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. For [4 + 2] cycloadditions, 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. 1995, 60, 2962-2963. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255-1275.
6. For representative examples, see: For [4 + 4] cycloadditions, Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4678. Wender, P. A.; Correia, C. R. D.; Ihle, N. C. J. Am. Chem. Soc. 1988, 110, 5904-5906. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. For [4 + 2] cycloadditions, 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. 1995, 60, 2962-2963. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255-1275.
7. For representative examples, see: For [4 + 4] cycloadditions, Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4678. Wender, P. A.; Correia, C. R. D.; Ihle, N. C. J. Am. Chem. Soc. 1988, 110, 5904-5906. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. For [4 + 2] cycloadditions, 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. 1995, 60, 2962-2963. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255-1275.
8. For representative examples, see: For [4 + 4] cycloadditions, Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4678. Wender, P. A.; Correia, C. R. D.; Ihle, N. C. J. Am. Chem. Soc. 1988, 110, 5904-5906. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. For [4 + 2] cycloadditions, 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. 1995, 60, 2962-2963. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255-1275.
9. 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 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 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 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 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. Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721. 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. Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976-10977. Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63, 4164-4165. Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc., in press.
15. Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721. 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. Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976-10977. Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63, 4164-4165. Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc., in press.
16. Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721. 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. Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976-10977. Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63, 4164-4165. Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc., in press.
17. Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721. 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. Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976-10977. Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63, 4164-4165. Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc., in press.
18. Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721. 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. Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976-10977. Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63, 4164-4165. Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc., in press.
19. Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721. 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. Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976-10977. Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63, 4164-4165. Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc., in press.
20. For lead references and the total synthesis, see: Evans, F. J., Ed. Naturally Occurring Phorbol Esters; CRC Press: Boca Raton, FL, 1986.
21. Hecker, E.; Schmidt, R. Fortschr. Chem. Org. Naturst. 1974, 31, 377. Wender, P. A.; Kogen, H.; Lee, H.-Y.; Munger, J. D.; Wilhelm, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8957-8958. Wender, P. A.; Rice, K. D.; Schnute, M. E. J. Am. Chem. Soc. 1997, 119, 7897-7898.
22. Hecker, E.; Schmidt, R. Fortschr. Chem. Org. Naturst. 1974, 31, 377. Wender, P. A.; Kogen, H.; Lee, H.-Y.; Munger, J. D.; Wilhelm, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8957-8958. Wender, P. A.; Rice, K. D.; Schnute, M. E. J. Am. Chem. Soc. 1997, 119, 7897-7898.
23. Hecker, E.; Schmidt, R. Fortschr. Chem. Org. Naturst. 1974, 31, 377. Wender, P. A.; Kogen, H.; Lee, H.-Y.; Munger, J. D.; Wilhelm, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8957-8958. Wender, P. A.; Rice, K. D.; Schnute, M. E. J. Am. Chem. Soc. 1997, 119, 7897-7898.
24. For lead references and the total synthesis, see: Wender, P. A.; Jesudason, C. D.; Nakahira, H.; Tamura, N.; Tebbe, A. L.; Ueno, Y. J. Am. Chem. Soc. 1997, 119, 12976-12977.
25. Takeuchi, N.; Fujita, T.; Goto, K.; Morisaki, N.; Osone, N.; Tobinaga, S. Chem. Pharm. Bull. 1993, 41, 923-925.
26. Koike, T.; Yamazaki, K.; Fukumoto, N.; Yashiro, K.; Takeuchi, N.; Tobinaga, S. Chem. Pharm. Bull. 1996, 44, 646-652.
27. The absolute stereochemistry of dictamnol was assigned by independent synthesis starting with chiral dione (S)-3,4,8,8a-tetrahydro-8aβ-methyl-2H,7H-naphthalene-1,6-dione, see ref 7.
28. Piet, D. P.; Orru, R. V. A.; Jenniskens, L. H. D.; Van de Harr, C.; Van Beek, T. A.; Franssen, M. C. R.; Wijnbere, J. B. P. A.; De Groot, A. Chem. Pharm. Bull. 1996, 44, 1400-1403.
29. Lange, G. L.; Merica, A.; Chimanikire, M. Tetrahedron Lett. 1997, 38, 6371-6374.
30. For general approaches to seven-membered ring synthesis, see: ref 2. Wender, P. A.; Love, J. A. In Advances in Cycloaddition; Harmata, M., Ed.; JAI Press: Stamford, CT, 1999; Vol. 5, pp 1-45. Nola, E.; Dzwiniel, T. L.; Schweibert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1998, 120, 9702-9703. Molander, G. A. Acc. Chem. Res. 1998, 31, 603-609.
31. For general approaches to seven-membered ring synthesis, see: ref 2. Wender, P. A.; Love, J. A. In Advances in Cycloaddition; Harmata, M., Ed.; JAI Press: Stamford, CT, 1999; Vol. 5, pp 1-45. Nola, E.; Dzwiniel, T. L.; Schweibert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1998, 120, 9702-9703. Molander, G. A. Acc. Chem. Res. 1998, 31, 603-609.
32. For general approaches to seven-membered ring synthesis, see: ref 2. Wender, P. A.; Love, J. A. In Advances in Cycloaddition; Harmata, M., Ed.; JAI Press: Stamford, CT, 1999; Vol. 5, pp 1-45. Nola, E.; Dzwiniel, T. L.; Schweibert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1998, 120, 9702-9703. Molander, G. A. Acc. Chem. Res. 1998, 31, 603-609.
33. Dauben, W. G.; Shaprio, G. J. Org. Chem. 1984, 49, 4252-4258. Crandall, J. K.; Ayers, T. A. J. Org. Chem. 1992, 57, 2993-2995.
34. Dauben, W. G.; Shaprio, G. J. Org. Chem. 1984, 49, 4252-4258. Crandall, J. K.; Ayers, T. A. J. Org. Chem. 1992, 57, 2993-2995.
35. Assignment of stereochemistry of 6 was based on correlation with (+)-dictamnol and analogy to model systems as described by Corey et al.: Corey, H. J.; Bakshi, R. K.; Shibata, S.; Chen, C.; Singh, V. K. J. Am. Chem. Soc. 1987, 109, 7925-7926. For an additional use of the model, see: Bach, J.; Berenger, R.; Farras, J.; Garcia, J.; Meseguer, J.; Vilarrasa, J. Tetrahedron: Asymmetry 1995, 6, 2683-2686.
36. Assignment of stereochemistry of 6 was based on correlation with (+)-dictamnol and analogy to model systems as described by Corey et al.: Corey, H. J.; Bakshi, R. K.; Shibata, S.; Chen, C.; Singh, V. K. J. Am. Chem. Soc. 1987, 109, 7925-7926. For an additional use of the model, see: Bach, J.; Berenger, R.; Farras, J.; Garcia, J.; Meseguer, J.; Vilarrasa, J. Tetrahedron: Asymmetry 1995, 6, 2683-2686.
37. 1H NMR analysis of the resulting diastereomeric mixture.
38. The minor isomer is the C-8 epimer of 7.
39. 2 (5 mol %) is added in one batch to a base-washed, oven-dried Schlenk flask under an argon atmosphere and is dissolved in oxygen-tree dichloroethane (50 mL). The solution is stirred for 5 min at room temperature, after which allene-vinylcyclopropane 6 (204 mg, 1.24 mmol) is added over 10 s and the solution is heated to 80 °C for 7 h. After cooling, the reaction mixture is filtered through a plug of alumina and concentrated. Flash chromatography (silica gel, 10% ethyl acetate in hexane) gives 154.1 mg of cycloadduct 7 in 76% yield (9:1 ratio of diastereomers favoring the desired C-8 epimer) as a colorless oil.
40. The relative and absolute stereochemistry of 7 was determined via decoupling and n.O.e. experiments, as well as by conversion to (+)-dictamnol.
41. The mechanism of the [5 + 2] cycloaddition has not been established and is proposed with the intention of aiding in the rationalization of the stereochemical outcome of the product. For additional discussion on the mechanism, see ref 3.
42. 6).