Synthesis of Aromatic Bisabolene Natural Products via Palladium-Catalyzed Cross-Couplings of Organozine Reagents

Journal of Organic Chemistry

Volumn 69, Issue 7, 2004, Pages 2461-2468

  Vyvyan, James R ^a   Loitz, Celeste ^a   Looper, Ryan E ^a   Mattingly, Cheryl S ^a   Peterson, Emily A ^a   Staben, Steven T ^a  

^a WESTERN WASHINGTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; DERIVATIVES; PALLADIUM; SYNTHESIS (CHEMICAL); ZINC;

NATURAL PRODUCTS; REAGENTS;

AROMATIC COMPOUNDS;

CURCUHYDROQUINONE; CURCUPHENOL; CURCUQUINONE; DEHYDRO ALPHA CURCUMENE; ELVIROL; GLANDULONE A; HELIANNUOL D; HYDROQUINONE DERIVATIVE; NATURAL PRODUCT; PALLADIUM; UNCLASSIFIED DRUG; ZINC;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; GAS CHROMATOGRAPHY; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

BIOLOGICAL PRODUCTS; CATALYSIS; INDICATORS AND REAGENTS; PALLADIUM; SESQUITERPENES; STEREOISOMERISM; ZINC;

EID: 1842608460     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035778s     Document Type: Article

References (104)

1. (a) Heathcock, C. H. In The Total Synthesis of Natural Products; ApSimon, J. W., Ed.; Wiley: New York, 1973; Vol. 2, p 197.
2. (b) Heathcock, C. H.; Graham, S. L.; Pirrung, M. C.; Plavac, F.; White, C. T. In The Total Synthesis of Natural Products; ApSimon, J. W., Ed.; Wiley and Sons: New York, 1981; Vol. 5, p 35.
3. (c) Pirrung, M. C.; Morehead, A. T. In The Total Synthesis of Natural Products; Goldsmith, D., Ed.; Wiley and Sons: New York, 1997; Vol. 10, p 29.
4. Selected recent examples of aromatic bisabolene synthesis: (a) Meyers, A. I.; Stoianova, D. J. Org. Chem. 1997, 62, 5219-5221.
5. (b) Kimachi, T.; Takemoto, Y. J. Org. Chem. 2001, 66, 2700-2704.
6. (c) Fuganti, C.; Serra, S. J. Chem. Soc., Perkin Trans. 1 2000, 3758-3764.
7. (d) Fuganti, C.; Serra, S.; Dulio, A. J. Chem. Soc., Perkin Trans. 1 1999, 279-282.
8. (e) Fuganti, C.; Serra, S. Synlett 1998, 1252-1254.
9. (f) Sugahara, T.; Ogasawara, K. Tetrahedron: Asymmetry 1998, 9, 2215-2217.
10. (g) Nagumo, S.; Irie, S.; Hayashi, K.; Akita, H. Heterocycles 1996, 43, 1175-1178.
11. (h) Ono, M.; Ogura, Y.; Hatogai, K.; Akita, H. Tetrahedron: Asymmetry 1995, 6, 1829-1832.
12. (i) Ono, M.; Yamamoto, Y.; Akita, H. Chem. Pharm. Bull. 1995, 43, 553-558.
13. (j) Ono, M.; Ogura, Y.; Hatogai, K.; Akita, H. Chem. Pharm. Bull. 2001, 49, 1581-1585.
14. (k) Ono, M.; Suzuki, K.; Tanikawa, S.; Akita, H. Tetrahedron: Asymmetry 2061, 12, 2597-2604.
15. (l) Sharma, M. L.; Chand, T. Indian J. Chem. 1997, 36B, 553-556.
16. (m) Sharma, M. L.; Chand, T. Tetrahedron Lett. 1996, 37, 2279-2280.
17. (n) Kad, G. L.; Khurana, A.; Singh, V.; Singh, J. J. Chem. Res., Synop. 1999, 164-165.
18. (o) Takabatake, K.; Nishi, I.; Shindo, M.; Shishido, K. J. Chem. Soc., Perkin Trans. 1 2000, 1807-1808.
19. (p) Sato, K.; Bando, T.; Shindo, M.; Shishido, K. Heterocycles 1999, 50, 11-15.
20. (q) Shishido, K.; Bando, T. J. Mol. Catal. B: Enzym. 1998, 5, 183-186.
21. (r) Tanaka, K.; Nuruzzaman, M.; Yoshida, M.; Asakawa, N.; Yang, X.-S.; Tsubaki, K.; Fuji, K. Chem. Pharm. Bull. 1999, 47, 1053-1055.
22. (s) Kimachi, T.; Takemoto, Y. J. Org. Chem. 2001, 66, 2700-2704.
23. (t) Ho, T.-L.; Ho, M.-F. J. Chin. Chem. Soc. 2001, 48, 879-881.
24. (u) Hagiwara, H.; Okabe, T.; Ono, H.; Kamat, V. P.; Hoshi, T.; Suzuki, T.; Ando, M. J. Chem. Soc., Perkin Trans. 1 2002, 895-900.
25. (v) Li, A.; Yue, G.; Li, Y.; Pan, X.; Yang, T.-K. Tetrahedron: Asymmetry 2003, 14, 75-78.
26. (w) Singh, V.; Khurana, A.; Kaur, I.; Sapehiyia, V.; Kad, G. L.; Singh, J. J. Chem. Soc., Perkin Trans. 1 2002, 1766-1768.
27. (x) Rowe, B. J.; Spilling, C. D. J. Org. Chem. 2003, 68, 9502-9505.
28. (a) Honwad, V. K.; Rao, A. S. Tetrahedron 1965, 21, 2593-2604.
29. (b) Damodaran, N. P.; Dev, S. Tetrahedron 1965, 21, 4113-4122.
30. Tomita, B.; Hirose, Y.; Nakatsuka, T. Mokuzai Gakkaishi 1969, 15, 46.
31. Sakai, T.; Nishimura, K.; Hirose, Y. Bull Chem. Soc. Jpn. 1965, 38, 381-387.
32. Honwad, V. K.; Rao, A. S. Tetrahedron 1964, 2921-2925.
33. (a) McEnroe, F. J.; Fenical, W. Tetrahedron 1978, 34, 1661-1664.
34. (b) Fusetani, N.; Sugano, M.; Matsunaga, S.; Hashimoto, K. Experentia 1987, 43, 1234-1235.
35. (c) Wright, A. E.; Pomponi, S. A.; McConnell, O. J.; Kohmoto, S.; McCarthy, P. J. J. Nat. Prod. 1987, 50, 976-978.
36. (d) Miller, S. L.; Tinto, W. F.; McLean, S.; Reynolds, W. F.; Yu, M. J. Nat. Prod. 1995, 58, 1116-1119.
37. (e) D'Armas, H. T.; Mootoo, B. S.; Reynolds, W. F. J. Nat. Prod. 2000, 63, 1593-1595.
38. (f) El Sayed, K. A.; Yousaf, M.; Harmann, M. T.; Avery, M. A.; Kelly, M. ; Wipf, P. J. Nat. Prod. 2002, 65, 1547-1553.
39. (a) Rimpler, H.; Hansel, R.; Kochendorfer, L. Z. Naturforsch. 1970, 25, 995;
40. Chem. Abstr. 1971, 74, 13288c.
41. (b) Aguilar, M. I.; Delgado, G.; Bye, R.; Linares, E. Phytochemistry 1993, 33, 1161-1163.
42. (c) Manguro, L. O. A.; Mukonyi, K. M.; Githiomi, J. K. Planta Med. 1996, 62, 84-85.
43. (d) Mata, R.; Martínez, E.; Bye, R.; Morales, G.; Singh, M. P.; Janso, J. E.; Maiese, W. M.; Timmermann, B. J. Nat. Prod. 2001, 64, 911-914.
44. (e) Lee, S. K.; Hong, C.-H.; Huh, S.-K.; Kim, S.-S.; Oh, O.-J.; Min, H.-Y.; Park, K.-K.; Chung, W.-Y.; Hwang, J.-K. J. Environ. Pathol. Toxicol. 2002, 21, 141-148.
45. (f) Hwang, J.-K.; Shim, J.-S.; Baek, N.-I.; Pyun, Y.-R. Planta Med. 2000, 66, 196-197.
46. (g) Aguilar, M. I.; Delgado, G.; Hernanadez, M.; Villarreal, M. L. Nat. Prod. Lett. 2001, 15, 93-101.
47. Imai, S.; Morikiyo, M.; Furihata, K.; Hayakana, Y.; Seto, H. Agric. Biol. Chem. 1990, 54, 2367.
48. Butler, M. S.; Capon, R. J.; Nadeson, R.; Beveridge, A. A. J. Nat. Prod. 1991, 54, 619-623.
49. (a) Bohlmann, F.; Grenz, M. Tetrahedron Lett. 1969, 1005-1006.
50. (b) Bohlmann, F.; Körnig, D. Chem. Ber. 1974, 107, 1777-1779.
51. (c) Dennison, N. R.; Mirrington, R. N.; Stuart, A. D. Aust. J. Chem. 1975, 28, 1339-1343.
52. Spring, O.; Rodon, U.; Macías, F. A. Phytochemistry 1992, 31, 1541-1544.
53. Harrison, B.; Crews, P. J. Org. Chem. 1997, 62, 2646-2648.
54. Chen, C.-Y.; Shen, Y.-C.; Chen, Y.-J.; Sheu, J.-H.; Duh, C.-Y. J. Nat. Prod. 1999, 62, 573-576.
55. (a) Vyvyan, J. R.; Looper, R. E. Tetrahedron Lett. 2000, 41, 1151-1154.
56. (b) J. R. Vyvyan; R. E. Looper; S. T. Staben, Division of Organic Chemistry Proceedings, 225th National ACS Meeting, March 23-27, 2003, New Orleans, LA. ORGN659.
57. (c) J. R. Vyvyan; J. M. Oaksmith; B. W. Parks, Division of Organic Chemistry Proceedings, 223rd National ACS Meeting, April 7-11, 2002, Orlando, FL. ORGN435.
58. Vyvyan, J. R. Tetrahedron 2002, 58, 1631-1646.
59. (a) Macías, F. A.; Varela, R. M.; Torres, A.; Molinillo, J. M. G. ; Fronczek, F. R. Tetrahedron Lett. 1993, 34, 1999-2002.
60. (b) Macías, F. A.; Molinillo, J. M. G.; Varela, R. M.; Torres, A. ; Fronczek, F. R. J. Org. Chem. 1994, 59, 8261-8266.
61. (c) Macías, F. A.; Varela, R. M.; Torres, A.; Molinillo, J. M. G. Tetrahedron Lett. 1999, 40, 4725-4728.
62. (d) Macías, F. A.; Varela, R. M.; Torres, A.; Molinillo, J. M. G. J. Nat. Prod. 1999, 62, 1636-1639.
63. (e) Macías, F. A.; Varela, R. M.; Torres, A.; Molinillo, J. M. G. J. Chem. Ecol. 2000, 26, 2173-2185.
64. (f) Macías, F. A.; Torres, A.; Galindo, J. L. G.; Varela, R. M.; Álvarez, J. A.; Molinillo, J. M. G. Phytochemistry 2002, 61, 687-692.
65. (a) Takabatake, K.; Nishi, I.; Shindo, M.; Shishido, K. J. Chem. Soc., Perkin Trans. 1 2000, 1807-1808.
66. (b) Sato, K.; Yoshimura, T.; Shindo, M.; Shishido, K. J. Org. Chem. 2001, 66, 309-314.
67. (c) Tuhina, K.; Bhowmik, D. R.; Venkateswaran, R. V. Chem. Commun. 2002, 634-635.
68. (d) Kishkuku, H.; Shindo, M.; Shishido, K. Chem. Commun. 2003, 350-351.
69. (e) Doi, F.; Ogamino, T.; Sugai, T.; Nishiyama, S. Synlett 2003, 411-413.
70. (f) Doi, F.; Ogamino, T.; Sugai, T.; Nishiyama, S. Tetrahedron Lett. 2003, 44, 4877-4880.
71. (g) Macías, F. A.; Chinchilla, D.; Molinillo, J. M. G.; Marin, D. ; Varela, R. M.; Torres, A. Tetrahedron 2003, 59, 1679-1683.
72. (h) Kamei, T.; Shindo, M.; Shishido, K. Tetrahedron Lett. 2003, 44, 8505-8507.
73. (a) Knochel, P.; Millot, N.; Rodriguez, A. L.; Tucker, C. E. Org. React. 2001, 58, 417-732.
74. (b) Negishi, E.-I. In Organozinc Reagents: A Practical Approach; Knochel, P., Jones, P. Eds.; Oxford: New York, 1999; Chapter 11.
75. (c) Erdik, E. Organozinc Reagents in Organic Synthesis; CRC Press: Boca Raton, 1996; pp 274-344.
76. McCague, R. Tetrahedron Lett. 1987, 28, 701-702.
77. 3, 75 MHz): δ 131.0, 125.1, 125.09, 37.1, 36.2, 35.0, 33.0, 31.6, 26.2, 26.1, 25.7, 17.6, 16.3, and 14.3. LRMS (EI): m/z (rel int) 222 (5, M+), 137 (5), 123 (5), 109 (60), 95 (20), 82 (95), 69(95), 55 (50), and 41 (100).
78. Sánchez, I. H.; Lemini, C.; Joseph-Nathan, P. J. Org. Chem. 1981, 46, 4666-4667.
79. Feutrill, G. I.; Mirrington, R. N. Aust. J. Chem. 1972, 25, 1719-1729.
80. Jacob, P., III; Callery, P. S.; Shulgin, A. T.; Castagnoli, N. J. Org. Chem. 1976, 41, 3627-3629.
81. Umbreit, M. A.; Sharpless, K. B. J. Am. Chem. Soc. 1977, 99, 5526-5528.
82. Chatterjee, A. K.; Grubbs, R. H. Angew. Chem., Int. Ed. 2002, 41, 3172-3174.
83. It is also possible to prepare Rieke zinc with substoichiometric amounts of naphthalene as electron carrier: Rieke, R. D.; Hanson, M. V. In Organozinc Reagents: A Practical Approach; Knochel, P., Jones, P. Eds.; Oxford: New York, 1999; Chapter 2. Since this portion of the work was completed, highly active Rieke zinc has become commercially available.
84. (a) Kamikubo, T.; Ogasawara, K. Chem. Commun. 1996, 1679-1680.
85. (b) Miller, M. W.; Johnson, C. R. J. Org. Chem. 1997, 62, 1582-1583.
86. (c) Graham, A. E.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 1997, 1087-1089.
87. (a) Ritter, K. Synthesis 1993, 735-762.
88. (b) Zimmer, R.; Webel, M.; Reissig, H.-U. J. Prakt. Chem. 1998, 340, 274-277.
89. (c) Cleve, A.; Fritzmeier, K.-H.; Heinrich, N.; Klar, U.; Müller-Fahrnow, A.; Neef, G.; Ottow, E.; Schwede, W. Tetrahedron 1996, 52, 1529-1542.
90. (a) Hawthorne, M. F. J. Org. Chem. 1957, 22, 1001.
91. (b) Simon, J.; Salzbrunn, S.; Surya Prakash, G. K.; Petasis, N. A.; Olah, G. A. J. Org. Chem. 2001, 66, 633-634.
92. Snieckus, V. Chem. Rev. 1990, 90, 879-933.
93. Ronald, R. C.; Winkle, M. R. Tetrahedron 1983, 39, 2031-2042.
94. General experimental procedures may be found in Supporting Information.
95. Ono, M.; Yamamoto, Y.; Todoriki, R.; Akita, H. Heterocycles 1994, 37, 181-185.
96. (a) Mori, K. Agric. Biol. Chem. 1972, 36, 503-505.
97. (b) Vig, O. P.; Bari, S. S.; Sharma, S. D.; Rana, S. S. Indian J. Chem. 1977, 15B, 1076-1077.
98. (c) Bellesia, F.; Ghelfi, F.; Pagnoni, U. M.; Pinetti, A. Gazz. Chim. Ital. 1992, 122, 437-439.
99. Khrimayan, A. P.; Makaryan, G. M.; Badanyan, S. O. Arm. Khim. Zh. 1986, 39, 574-580; Chem. Abstr. 108, 5609.
100. Khrimayan, A. P.; Makaryan, G. M.; Badanyan, S. O. Arm. Khim. Zh. 1986, 39, 574-580; Chem. Abstr. 108, 5609.
101. Dalby, K. N.; Kirby, A. J.; Hollfelder, F. J. Chem. Soc., Perkin Trans. 2 1993, 1269-1281.
102. (a) Rathore, R.; Kochi, J. K. J. Org. Chem. 1995, 60, 7479-7490.
103. (b) Hauser, F. M.; Ganguly, D. J. Org. Chem. 2000, 65, 1842-1849.
104. Carreño, M. C.; Garcia Ruano, J. L.; Sanz, G.; Toledo, M. A.; Urbano, A. J. Org. Chem. 1995, 60, 5328-5331.