Rhodium(II)-Catalyzed Decomposition of 1-Diazo-4-(1- or 2-naphthyl)-2-butanones as a New Route to Rearranged Pimarane and Abietane Skeleta. Synthesis of Umbrosone

Journal of Organic Chemistry

Volumn 62, Issue 19, 1997, Pages 6658-6665

  Manitto, Paolo ^a   Monti, Diego ^a   Zanzola, Simona ^a   Speranza, Giovanna ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 BUTANONE; ABIETIC ACID; ANTHRACENE DERIVATIVE; AROMATIC COMPOUND; CYCLOPROPANE; DITERPENOID; PHENANTHRENE DERIVATIVE; RHODIUM; RHODIUM TETRAACETATE; UMBROSONE; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; CATALYST; CHEMICAL REACTION; DECOMPOSITION; DRUG SYNTHESIS; MOLECULAR INTERACTION; NONHUMAN; PLANT ROOT; REACTION ANALYSIS;

EID: 0030756304     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970631k     Document Type: Article

References (80)

1. Hanson, J. R. Nat. Prod. Rep. 1996, 13, 59 and references cited therein. Hanson, J. R. In Rodd's Chemistry of Carbon Compounds, 2nd ed.; Sainsbury, M., Ed.; Elsevier: Amsterdam, 1994; 2nd Supplement, pp 419-439.
2. Hanson, J. R. Nat. Prod. Rep. 1996, 13, 59 and references cited therein. Hanson, J. R. In Rodd's Chemistry of Carbon Compounds, 2nd ed.; Sainsbury, M., Ed.; Elsevier: Amsterdam, 1994; 2nd Supplement, pp 419-439.
3. Campbell, W. P.; Todd, D. J. Am. Chem. Soc. 1942, 64, 928.
4. King, F. E.; King, T. J.; Topliss, J. G. J. Chem. Soc. 1957, 573.
5. Tanaka, N.; Sakai, H.; Murakami, T.; Saiki, Y.; Chen, C.-M.; Iitaka, Y. Chem. Pharm. Bull. 1986, 34, 1015.
6. Meng, Q.; Hesse, M. Helv. Chim. Acta 1990, 73, 455.
7. Goldsmith, D. The Total Synthesis of Tri- and Tetracyclic Diterpenes. In The Total Synthesis of Natural Products; ApSimon, J., Ed.; Wiley Interscience Publisher: New York, 1992; Vol. 8, p 1.
8. CB → A sequence (Robinson annulation). Reviews: Jung, M. E. Tetrahedron 1976, 32, 3. Gawley, R. E. Synthesis 1976, 777. Inter alia cf. (a) Welch, S. C.; Hogan, C. P.; Kim, J. H.; Chu, P. S. J. Org. Chem. 1977, 42, 2879. (b) Sinha, G.; Maji, S. K.; Ghatak, U. R.; Mukherjee, M.; Mukherjee, A. K.; Chakravarty, A. K. J. Chem. Soc., Perkin Trans. 1 1983, 2519. D'Angelo, J.; Revial, G.; Volpe, T.; Pfau, M. Tetrahedron Lett. 1988, 29, 4427. Nerinckx, W.; Vandewalle, M. Tetrahedron: Asymmetry 1990, 1, 265. (e) Chiu, C. K.-F.; Govindan, S. V.; Fuchs, P. L. J. Org. Chem. 1994, 59, 311. (f) (Wenkert annulation) Wenkert, E.; Stevens, T. E. J. Am. Chem. Soc. 1956, 78, 2318. (g) (acid catalyzed cyclization) Karpha, T. K.; Basu, B. Synth. Commun. 1992, 22, 1505.
9. CB → A sequence (Robinson annulation). Reviews: Jung, M. E. Tetrahedron 1976, 32, 3. Gawley, R. E. Synthesis 1976, 777. Inter alia cf. (a) Welch, S. C.; Hogan, C. P.; Kim, J. H.; Chu, P. S. J. Org. Chem. 1977, 42, 2879. (b) Sinha, G.; Maji, S. K.; Ghatak, U. R.; Mukherjee, M.; Mukherjee, A. K.; Chakravarty, A. K. J. Chem. Soc., Perkin Trans. 1 1983, 2519. D'Angelo, J.; Revial, G.; Volpe, T.; Pfau, M. Tetrahedron Lett. 1988, 29, 4427. Nerinckx, W.; Vandewalle, M. Tetrahedron: Asymmetry 1990, 1, 265. (e) Chiu, C. K.-F.; Govindan, S. V.; Fuchs, P. L. J. Org. Chem. 1994, 59, 311. (f) (Wenkert annulation) Wenkert, E.; Stevens, T. E. J. Am. Chem. Soc. 1956, 78, 2318. (g) (acid catalyzed cyclization) Karpha, T. K.; Basu, B. Synth. Commun. 1992, 22, 1505.
10. CB → A sequence (Robinson annulation). Reviews: Jung, M. E. Tetrahedron 1976, 32, 3. Gawley, R. E. Synthesis 1976, 777. Inter alia cf. (a) Welch, S. C.; Hogan, C. P.; Kim, J. H.; Chu, P. S. J. Org. Chem. 1977, 42, 2879. (b) Sinha, G.; Maji, S. K.; Ghatak, U. R.; Mukherjee, M.; Mukherjee, A. K.; Chakravarty, A. K. J. Chem. Soc., Perkin Trans. 1 1983, 2519. D'Angelo, J.; Revial, G.; Volpe, T.; Pfau, M. Tetrahedron Lett. 1988, 29, 4427. Nerinckx, W.; Vandewalle, M. Tetrahedron: Asymmetry 1990, 1, 265. (e) Chiu, C. K.-F.; Govindan, S. V.; Fuchs, P. L. J. Org. Chem. 1994, 59, 311. (f) (Wenkert annulation) Wenkert, E.; Stevens, T. E. J. Am. Chem. Soc. 1956, 78, 2318. (g) (acid catalyzed cyclization) Karpha, T. K.; Basu, B. Synth. Commun. 1992, 22, 1505.
11. CB → A sequence (Robinson annulation). Reviews: Jung, M. E. Tetrahedron 1976, 32, 3. Gawley, R. E. Synthesis 1976, 777. Inter alia cf. (a) Welch, S. C.; Hogan, C. P.; Kim, J. H.; Chu, P. S. J. Org. Chem. 1977, 42, 2879. (b) Sinha, G.; Maji, S. K.; Ghatak, U. R.; Mukherjee, M.; Mukherjee, A. K.; Chakravarty, A. K. J. Chem. Soc., Perkin Trans. 1 1983, 2519. D'Angelo, J.; Revial, G.; Volpe, T.; Pfau, M. Tetrahedron Lett. 1988, 29, 4427. Nerinckx, W.; Vandewalle, M. Tetrahedron: Asymmetry 1990, 1, 265. (e) Chiu, C. K.-F.; Govindan, S. V.; Fuchs, P. L. J. Org. Chem. 1994, 59, 311. (f) (Wenkert annulation) Wenkert, E.; Stevens, T. E. J. Am. Chem. Soc. 1956, 78, 2318. (g) (acid catalyzed cyclization) Karpha, T. K.; Basu, B. Synth. Commun. 1992, 22, 1505.
12. CB → A sequence (Robinson annulation). Reviews: Jung, M. E. Tetrahedron 1976, 32, 3. Gawley, R. E. Synthesis 1976, 777. Inter alia cf. (a) Welch, S. C.; Hogan, C. P.; Kim, J. H.; Chu, P. S. J. Org. Chem. 1977, 42, 2879. (b) Sinha, G.; Maji, S. K.; Ghatak, U. R.; Mukherjee, M.; Mukherjee, A. K.; Chakravarty, A. K. J. Chem. Soc., Perkin Trans. 1 1983, 2519. D'Angelo, J.; Revial, G.; Volpe, T.; Pfau, M. Tetrahedron Lett. 1988, 29, 4427. Nerinckx, W.; Vandewalle, M. Tetrahedron: Asymmetry 1990, 1, 265. (e) Chiu, C. K.-F.; Govindan, S. V.; Fuchs, P. L. J. Org. Chem. 1994, 59, 311. (f) (Wenkert annulation) Wenkert, E.; Stevens, T. E. J. Am. Chem. Soc. 1956, 78, 2318. (g) (acid catalyzed cyclization) Karpha, T. K.; Basu, B. Synth. Commun. 1992, 22, 1505.
13. CB → A sequence (Robinson annulation). Reviews: Jung, M. E. Tetrahedron 1976, 32, 3. Gawley, R. E. Synthesis 1976, 777. Inter alia cf. (a) Welch, S. C.; Hogan, C. P.; Kim, J. H.; Chu, P. S. J. Org. Chem. 1977, 42, 2879. (b) Sinha, G.; Maji, S. K.; Ghatak, U. R.; Mukherjee, M.; Mukherjee, A. K.; Chakravarty, A. K. J. Chem. Soc., Perkin Trans. 1 1983, 2519. D'Angelo, J.; Revial, G.; Volpe, T.; Pfau, M. Tetrahedron Lett. 1988, 29, 4427. Nerinckx, W.; Vandewalle, M. Tetrahedron: Asymmetry 1990, 1, 265. (e) Chiu, C. K.-F.; Govindan, S. V.; Fuchs, P. L. J. Org. Chem. 1994, 59, 311. (f) (Wenkert annulation) Wenkert, E.; Stevens, T. E. J. Am. Chem. Soc. 1956, 78, 2318. (g) (acid catalyzed cyclization) Karpha, T. K.; Basu, B. Synth. Commun. 1992, 22, 1505.
14. CB → A sequence (Robinson annulation). Reviews: Jung, M. E. Tetrahedron 1976, 32, 3. Gawley, R. E. Synthesis 1976, 777. Inter alia cf. (a) Welch, S. C.; Hogan, C. P.; Kim, J. H.; Chu, P. S. J. Org. Chem. 1977, 42, 2879. (b) Sinha, G.; Maji, S. K.; Ghatak, U. R.; Mukherjee, M.; Mukherjee, A. K.; Chakravarty, A. K. J. Chem. Soc., Perkin Trans. 1 1983, 2519. D'Angelo, J.; Revial, G.; Volpe, T.; Pfau, M. Tetrahedron Lett. 1988, 29, 4427. Nerinckx, W.; Vandewalle, M. Tetrahedron: Asymmetry 1990, 1, 265. (e) Chiu, C. K.-F.; Govindan, S. V.; Fuchs, P. L. J. Org. Chem. 1994, 59, 311. (f) (Wenkert annulation) Wenkert, E.; Stevens, T. E. J. Am. Chem. Soc. 1956, 78, 2318. (g) (acid catalyzed cyclization) Karpha, T. K.; Basu, B. Synth. Commun. 1992, 22, 1505.
15. CB → A sequence (Robinson annulation). Reviews: Jung, M. E. Tetrahedron 1976, 32, 3. Gawley, R. E. Synthesis 1976, 777. Inter alia cf. (a) Welch, S. C.; Hogan, C. P.; Kim, J. H.; Chu, P. S. J. Org. Chem. 1977, 42, 2879. (b) Sinha, G.; Maji, S. K.; Ghatak, U. R.; Mukherjee, M.; Mukherjee, A. K.; Chakravarty, A. K. J. Chem. Soc., Perkin Trans. 1 1983, 2519. D'Angelo, J.; Revial, G.; Volpe, T.; Pfau, M. Tetrahedron Lett. 1988, 29, 4427. Nerinckx, W.; Vandewalle, M. Tetrahedron: Asymmetry 1990, 1, 265. (e) Chiu, C. K.-F.; Govindan, S. V.; Fuchs, P. L. J. Org. Chem. 1994, 59, 311. (f) (Wenkert annulation) Wenkert, E.; Stevens, T. E. J. Am. Chem. Soc. 1956, 78, 2318. (g) (acid catalyzed cyclization) Karpha, T. K.; Basu, B. Synth. Commun. 1992, 22, 1505.
16. CB → A sequence (Robinson annulation). Reviews: Jung, M. E. Tetrahedron 1976, 32, 3. Gawley, R. E. Synthesis 1976, 777. Inter alia cf. (a) Welch, S. C.; Hogan, C. P.; Kim, J. H.; Chu, P. S. J. Org. Chem. 1977, 42, 2879. (b) Sinha, G.; Maji, S. K.; Ghatak, U. R.; Mukherjee, M.; Mukherjee, A. K.; Chakravarty, A. K. J. Chem. Soc., Perkin Trans. 1 1983, 2519. D'Angelo, J.; Revial, G.; Volpe, T.; Pfau, M. Tetrahedron Lett. 1988, 29, 4427. Nerinckx, W.; Vandewalle, M. Tetrahedron: Asymmetry 1990, 1, 265. (e) Chiu, C. K.-F.; Govindan, S. V.; Fuchs, P. L. J. Org. Chem. 1994, 59, 311. (f) (Wenkert annulation) Wenkert, E.; Stevens, T. E. J. Am. Chem. Soc. 1956, 78, 2318. (g) (acid catalyzed cyclization) Karpha, T. K.; Basu, B. Synth. Commun. 1992, 22, 1505.
17. AB → C sequence; inter alia cf. (a) Spencer, T. A.; Weaver, T. D.; Villarica, R. M.; Friary, R. J.; Posler, J.; Schwartz, M. A. J. Org. Chem. 1968, 33, 712. (b) Spencer, T. A.; Friary, R. J.; Schmiegel, W. W.; Simeone, J. S.; Watt, D. S. J. Org. Chem. 1968, 33, 719.
18. AB → C sequence; inter alia cf. (a) Spencer, T. A.; Weaver, T. D.; Villarica, R. M.; Friary, R. J.; Posler, J.; Schwartz, M. A. J. Org. Chem. 1968, 33, 712. (b) Spencer, T. A.; Friary, R. J.; Schmiegel, W. W.; Simeone, J. S.; Watt, D. S. J. Org. Chem. 1968, 33, 719.
19. AC → B sequence, inter alia cf: (a) Sone, T.; Terashima, S.; Yamada, S.-I. Chem. Pharm. Bull. 1976, 24, 1273. (b) Wisocka, W.; Canonne, P.; Leicht, L. C. Synthesis 1977, 261. Hao, X. J.; Node, M.; Fuji, K. J. Chem. Soc., Perkin Trans. 1 1992, 1505.
20. AC → B sequence, inter alia cf: (a) Sone, T.; Terashima, S.; Yamada, S.-I. Chem. Pharm. Bull. 1976, 24, 1273. (b) Wisocka, W.; Canonne, P.; Leicht, L. C. Synthesis 1977, 261. Hao, X. J.; Node, M.; Fuji, K. J. Chem. Soc., Perkin Trans. 1 1992, 1505.
21. AC → B sequence, inter alia cf: (a) Sone, T.; Terashima, S.; Yamada, S.-I. Chem. Pharm. Bull. 1976, 24, 1273. (b) Wisocka, W.; Canonne, P.; Leicht, L. C. Synthesis 1977, 261. Hao, X. J.; Node, M.; Fuji, K. J. Chem. Soc., Perkin Trans. 1 1992, 1505.
22. (e) Schultz, A. G.; Wang, A. J. Org. Chem. 1996, 61, 4857 and references cited therein.
23. C → BA sequence: (a) Stork, G.; Gregson, M. J. Am. Chem. Soc. 1969, 91, 2373. (b) Smith, A. B., III; Dieter, R. K. J. Am. Chem. Soc. 1981, 103, 2017.
24. C → BA sequence: (a) Stork, G.; Gregson, M. J. Am. Chem. Soc. 1969, 91, 2373. (b) Smith, A. B., III; Dieter, R. K. J. Am. Chem. Soc. 1981, 103, 2017.
25. Reductive methylation of phenanthrene: Spanevello, R. A.; Gonzalez-Sierra, M.; McChesney, J. D. Synth. Commun. 1993, 23, 2463 and references cited therein.
26. CB → A sequence: Touboul, E.; Brienne, M.-J.; Jacques, J. J. Chem. Res. Synop. 1977, 106.
27. AC → B sequence: Wang, X.-L.; Cui, Y.-X.; Pan, X.-F. Tetrahedron Lett. 1994, 35, 423.
28. Matsumoto, T.; Tanaka, Y.; Terao, H.; Takeda, Y.; Wada, M. Chem. Pharm. Bull. 1993, 41, 1960.
29. Manitto, P.; Monti, D.; Speranza, G. J. Org. Chem. 1995, 60, 484.
30. (a) Kennedy, M.; McKervey, M. A.; Maguire, A. R.; Tuladhar, S. M.; Twohig, M. F. J. Chem. Soc., Perkin Trans. 1 1990, 1047.
31. (b) Doyle, M. P.; Protopopova, M. N.; Peterson, C. S.; Vitale, J. P.; McKervey, M. A.; Garcia, C. F. J. Am. Chem. Soc. 1996, 118, 7865 and references cited therein.
32. Throughout this work α-diazo ketones were prepared from the corresponding 3-arylpropionic acids via the standard procedure for conversion to the acyl chloride followed by treatment with ethereal diazomethane. Cf. Scott, L. T.; Sumpter, C. A. Organic Syntheses; Wiley, New York, 1990; Vol. 69, pp 180-187.
33. Trost, B. M.; Hiroi, K.; Kurozumi, S. J. Am. Chem. Soc. 1975, 97, 438.
34. (a) Barton, D. H. R.; De Mayo, P.; Shafiq, M. J. Chem. Soc. 1958, 140.
35. (b) Shoulders, B. A.; Kwie, W. W.; Klyne, W.; Gardner, P. D. Tetrahedron 1965, 21, 2973.
36. (c) Dasgupta, S. K.; Sarma, A. S. Tetrahedron 1973, 29, 309.
37. (d) Wong, H. N. C.; Hon, M.-Y.; Tse, C.-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165 and references cited therein.
38. (a) Doyle, M. P. Acc. Chem. Res. 1986, 19, 348.
39. (b) Chem. Rev. 1986, 86, 919.
40. (a) Meng, Q.; Zhu, N.; Chen, W. Phytohemistry 1988, 27, 1151.
41. (b) Delle Monache, F.; Delle Monache, G.; Gacs-Baits, E.; Coelho, J. D. B.; De Albuquerque, I. L.; Chiappeta, A. D. A.; De Mello, J. F. Phytochemistry 1990, 29, 3971.
42. (c) Gosh, K.; Gathak, U. R. Tetrahedron Lett. 1994, 35, 5943.
43. (d) Matsumoto, T.; Takeda, I.; Usui, S.; Imai, S. Chem. Pharm. Bull. 1996, 44, 530.
44. (e) Matsumoto, T.; Takeda, I.; Soh, K., Gotoh, H.; Imai, S. Chem. Pharm. Bull. 1996, 44, 1318.
45. Newman, M. S.; Dhawan, B.; Tuncay, A. J. Org. Chem. 1976, 41, 3924.
46. (a) Melpolder, J. B.; Heck, R. F. J. Org. Chem. 1976, 41, 265.
47. (b) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2 and references cited therein.
48. (a) Britten, A.; Njau, E. J. Chem. Soc., Perkin Trans. 1 1976, 158.
49. (b) Njau, E. Aust. J. Chem. 1976, 29, 2731.
50. 14,26b-e
51. (a) Karanatsios, D.; Scarpa, J. S.; Eugster, C. H. Helv. Chim. Acta 1966, 49, 1151.
52. (b) Tahara, A.; Akita, H.; Takizawa, T. Tetrahedron Lett. 1974, 2837.
53. (c) Matsumoto, T.; Imoi, S.; Masuda, H.; Fukui, K. Chem. Lett. 1974, 1001.
54. (d) Banerjee, A. K.; Carrasco, M. C.; Pena, M. C. A. Tetrahedron 1990, 46, 4133.
55. (e) Matsumoto, T.; Takeda, Y.; Soh, K.; Matsumura, H.; Imai, S. Chem. Pharm. Bull. 1996, 44, 1588.
56. (a) Wenkert, E.; Afonso, A.; Brendberg, J. B-son; Kaneko, C.; Tahara, A. J. Am. Chem. Soc. 1964, 86, 2038.
57. (b) Nakanishi, K.; Goto, T.; Ito, S.; Natori, S.; Nozoe, S. Natural Products Chemistry, Vol. 1; Academic Press: New York, 1974, p 193.
58. (a) Doyle, M. P. Recl. Trav. Chim. Pays-Bas 1991, 110, 305.
59. (b) Doyle, M. P. Asymmetric Cyclopropanation in Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1995.
60. (c) Doyle, M. P. Aldrichimica Acta 1996, 29, 3.
61. 9e
62. Lambert, J. B.; Fabricius, D. M.; Hoard, J. A. J. Org. Chem. 1979, 44, 1480.
63. (a) Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765.
64. (b) Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385.
65. (c) Padwa, A.; Austin, D. J.; Price, A. T.; Semones, M. A.; Doyle, M. P.; Protopopova, M. N.; Winchester, W. R.; Tran, A. J. Am. Chem. Soc. 1993, 115, 8669.
66. (a) Cane, D. E.; Thomas, P. J. J. Am. Chem. Soc. 1984, 106, 5295.
67. (b) Ceccherelli, P.; Curini, M.; Marcotullio, M. C.; Rosati, O. Tetrahedron 1991, 47, 7403.
68. (a) Alonso, M. E.; Garcia, M. J. Org. Chem. 1985, 50, 988.
69. (b) Alonso, M.; Fernandez, R. Tetrahedron 1989, 45, 3313.
70. (a) Hrytsak, M.; Etkin, N.; Durst, T. Tetrahedron Lett. 1986, 27, 5679.
71. (b) Taber, D. F.; Ruckle, R. E. J. Am. Chem. Soc. 1986, 108, 7686.
72. (c) Nakatani, K. Tetrahedron Lett. 1987, 28, 165.
73. (d) Hrystak, M.; Durst, T. J. Chem. Soc., Chem. Commun. 1987, 1150.
74. (a) Doyle, M. P.; Shanklin, M. S.; Pho, H. Q.; Mahapatro, S. N. J. Org. Chem. 1988, 53, 1017.
75. (b) Rosenfeld, M. J.; Ravi Shankar, B. F.; Shechter, M. J. Org. Chem. 1988, 53, 2699.
76. (a) Liebman, J. F.; Greenberg, A. Chem. Rev. 1989, 89, 1225.
77. (b) Lew, C. S. Q. J. Chem. Soc., Chem. Commun. 1995, 175 and references cited therein.
78. (a) Cotton, F. A.; Deboer, B. G.; Laprade, H. D.; Pipal, J. R.; Ucko, D. A. Acta Crystallogr. 1971, B27, 1664.
79. (b) Padwa, A.; Austin, D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797.
80. Effenberger, F.; Wonner, J. Chem. Ber. 1992, 125, 2583.