Tandem [4+2]/[3+2] cycloadditions of nitroalkenes. 9. Synthesis of (-)-rosmarinecine

Journal of the American Chemical Society

Volumn 118, Issue 35, 1996, Pages 8266-8277

  Denmark, Scott E ^a   Thorarensen, Atli ^a   Middleton, Donald S ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ROSMARINECINE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0029789934     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961630x     Document Type: Article

References (122)

1. (a) Leonard, N. J. In The Alkaloids; Manske, R. H. F., Holmes, H. L., Eds.; Academic Press: New York, 1950; Vol. 1, Chapter 4.
2. (b) Leonard, N. J. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1960; Vol. 6, Chapter 3.
3. (c) Warren, F. L. Fortschr. Chem. Org. Naturst. 1955, 12, 198.
4. (d) Warren, F. L. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1970; Vol. 12, Chapter 4.
5. (e) Natural Occuring Pyrrolizidine Alkaloids; Rizk, A-F. M., Ed.; CRC: Boston, 1991.
6. (f) Bull, L. B.; Culvenor, C. C. J.; Dick, A. T. The Pyrrolizidine Alkaloids; North-Holland Publishing Co. Amsterdam, The Netherlands, 1968.
7. (g) Pyrrolizidine Alkaloids; Enviromental Health Organization: Geneva, Switzerland, 1988.
8. (h) Mattocks, A. R. Chemistry and Toxicology of Pyrrolizidine Alkaloids; Academic Press: New York, 1986.
9. (i) Robins, D. J. Nat. Prod. Rep. 1995, 12, 413.
10. (j) Robins, D. J. Nat. Prod. Rep. 1994, 11, 613.
11. (k) Robins, D. J. Nat. Prod. Rep. 1993, 10, 487.
12. (l) Robins, D. J. Nat. Prod. Rep. 1992, 9, 313.
13. (m) Robins, D. J. Nat. Prod. Rep. 1991, 8, 213.
14. (n) Robins, D. J. Nat. Prod. Rep. 1990, 7, 377.
15. (o) Robins, D. J. Nat. Prod. Rep. 1989, 6, 577.
16. (p) Robins, D. J. Nat. Prod. Rep. 1989, 6, 221.
17. (q) Robins, D. J. Fortschr. Chem. Org. Naturst. 1982, 41, 116.
18. (a) Waal, H. L. Nature 1940, 146, 777.
19. (b) Waal, H. L. Onderst. J. Vet. Sci. An. Ind. 1940, 15, 241.
20. (c) Waal, H. L. Onderst. J. Vet. Sci. An. Ind. 1941, 16, 149.
21. Dry, L. J.; Koekemoer, M. J.; Warren, F. L. J. Chem. Soc. 1955, 59.
22. Adams, R.; Hamlin, K. E., Jr. J. Am. Chem. Soc. 1942, 64, 2597.
23. Freer, A. A.; Kelly, H. A.; Robins, D. J. Acta Cryst. C 1986, 42, 1348.
24. Kunec, E. K.; Robins, D. J. J. Chem. Soc., Chem. Commun. 1986, 250.
25. Roitman, J. N. Aust. J. Chem. 1983, 36, 1203.
26. Lu, S.-T.; Lin, C.-N.; Wu, T.-S.; Shieh, D.-C. J. Chin. Chem. Soc. 1972, 19, 127.
27. Edgar, J. A.; Cockrum, P. A.; Frahn, J. L. Experientia 1976, 15, 1535.
28. Richardson, M. F.; Warren, F. L. J. Chem. Soc. 1943, 452.
29. Hughes, C. A.; Gordon-Gray, C. G.; Schlosser, F. D.; Warren, F. L. J. Chem. Soc. 1965, 2370.
30. Porter, L. A.; Geissman, T. A. J. Org. Chem, 1962, 27, 4132.
31. (a) Were, O.; Benn, M.; Munavu, R. M. J. Nat. Prod. 1991, 54, 491.
32. (b) Were, O.; Benn, M.; Munavu, R. M. Phytochemistry 1993, 32, 1595.
33. (a) Kelly, H. A.; Robins, D. J. J. Chem. Soc., Perkin Trans. 1 1987, 177.
34. (b) Kelly, H. A.; Robins, D. J. J. Chem. Soc. Perkin Trans. 1 1987, 2195.
35. (c) Kelly, H. A.; Robins, D. J. J. Chem. Soc., Chem. Commun. 1988, 329.
36. (d) Kunec, E. K.; Robins, D. J. J. Chem. Soc., Perkin Trans. 1 1989, 1437.
37. (e) Denholm, A. A.; Kelly, H. A.; Robins, D. J. J. Chem. Soc., Perkin Trans. 1 1991, 2003
38. (a) Robins, D. J. Chem. Soc. Rev. 1989, 18, 375.
39. (b) Robins, D. J. The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1995; Vol. 46, Chapter 1.
40. (a) Ikeda, M.; Sato, T.; Ishibashi, H. Heterocycles 1988, 27, 1465.
41. (b) Dai, W.-M.; Nagao, Y. Heterocycles 1990, 30, 1231.
42. (c) Wróbel, J. T. The Alkaloids: Brossi, A., Ed.; Academic Press: New York, 1985; Vol. 26, Chapter 7.
43. Tatsuta, K.; Takahashi, H.; Amemiya, Y.; Kinoshita, M. J. Am. Chem. Soc. 1983, 105, 4096.
44. Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137.
45. (a) Denmark, S. E.; Moon, Y.-C.; Senanayake, C. B. W. J. Am. Chem. Soc. 1990, 112, 311.
46. (b) Denmark, S. E.; Senanayake, C. B. W.; Ho, G. D. Tetrahedron 1990, 46, 4857.
47. (c) Denmark, S. E.; Senanayake, C. B. W. J. Org. Chem. 1993, 58, 1853.
48. (d) Denmark, S. E.; Schnute, M. E.; Senanayake, C. B. W. J. Org. Chem. 1993, 58, 1859.
49. (e) Denmark, S. E.; Schnute, M. E.; Marcin, L. R.; Thorarensen, A. J. Org. Chem. 1995, 60, 3205.
50. Denmark, S. E.; Thorarensen, A. J. Org. Chem. 1994, 59, 5672.
51. Preliminary communication: Denmark, S. E.; Thorarensen, A.; Middleton, D. S. J. Org. Chem. 1995, 60, 3574.
52. Kraus, G. A.; Thurston, J.; Thomas, P. J.; Jacobson, R. A.; Su, Y. Tetrahedron Lett. 1988, 29, 1879.
53. Babievskii, K. K.; Belikov, V. M.; Tikhohova, N. A. Izv. Akad. Nauk SSSR, Ser Kim. 1970, 5, 1161.
54. (a) Maruoka, K.; Itoh, T.; Yamamoto, H. J. Am. Chem. Soc. 1985, 107, 4573.
55. (b) Nonoshita, K.; Banno, H.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1990, 112, 316.
56. (c) Maruoka, K.; Ooi, T.; Yamamoto, H. J. Am. Chem. Soc. 1990, 112, 9011.
57. (d) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310.
58. (a) Comins, D. L.; Salvador, J. M. J. Org. Chem. 1993, 58, 4656.
59. (b) Comins, D. L.; Salvador, J. M. Tetrahedron Lett. 1993, 34, 801.
60. (c) Comins, D. L.; LaMunyon, D. H. Tetrahedron Lett. 1994, 35, 7343
61. Denmark, S. E.; Thorarensen, A. J. Org. Chem. 1996, in press.
62. The enantiomeric ratio was determined on the 4-nitrobenzoate 50 by a sequence analogous to Scheme 11.
63. Schnute, M. E. Ph.D. Thesis, University of Illinois at Urbana - Champaign, Urbana, IL, 1995; pp 21-23.
64. This was verified by the failure of 32 to undergo the desired hydrogenolysis.
65. (a) Hijfte, L. V.; Little, R. D.; Petersen, J. L.; Moeller, K. D. J. Org. Chem. 1987, 52, 4647.
66. (b) Ley, S. V.; Santafianos, D.; Blaney, W. M.; Simmonds, M. S. J. Tetrahedron Lett. 1987, 28, 221.
67. (c) Nakata, T.; Saito, K.; Oishi, T. Tetrahedron Lett. 1986, 27, 6345.
68. (d) Corey, E. J.; Albonico, S. M.; Koelliker, U.; Schaaf, T. K.; Varma, R. K. J. Am. Chem. Soc. 1971, 93, 1490.
69. (e) Yoon, N. M.; Gyoung, Y. S. J. Org. Chem. 1985, 50, 2443.
70. Review: (f) Winterfeldt, E. Synthesis 1975, 617.
71. (a) Walker, E. R. H. Chem. Soc. Rev. 1976, 5, 23.
72. (b) Brown, H. C.; Krishnamurthy, S. Tetrahedron 1979, 35, 567.
73. (c) Barrett, A. G. M. In Comprehensive Chemistry, Reductions; Fleming, I., Ed.; Pergamon Press: Oxford 1991; Vol. 8, Chapter 1.10.
74. (a) Doria, C.; Gaio, P.; Gandolfi, C. Tetrahedron Lett. 1972, 4307.
75. (b) Klötzer, W.; Teitel, S.; Brossi, A. Helv. Chim. Acta 1971, 54, 2057.
76. (c) Disselnkötter, H.; Lieb, F.; Oediger, H.; Wendisch, D. Liebigs Ann. Chem. 1982, 150.
77. (d) Hohlbrugger, R.; Klötzer, W. Chem. Ber. 1979, 112, 849.
78. (a) Hung, H.-K.; Lam, H.-Y.; Niemczura, W.; Wang, M.-C.; Wong, C.-M. Can. J. Chem. 1978, 56, 638.
79. (b) Tokoroyama, T.; Matsuo, K.; Kotsuki, H.; Kanazawa, R. Tetrahedron 1980, 36, 3377.
80. (a) Bartsch, H.; Schwarz, O. J. Heterocycl. Chem. 1982, 19, 1189.
81. (b) Kanazawa, R.; Tokoroyama, T. Synthesis 1976, 526.
82. (a) Girotra, N. N.; Wendler, N. L. Tetrahedron Lett. 1975, 227.
83. (b) Nicolaou, K. C.; Seitz, S. P.; Pavia, M. R. J. Am. Chem. Soc. 1981, 103, 1222.
84. (c) Tsuda, Y.; Yoshimoto, K.; Yamashita, T.; Kaneda, M. Chem. Pharm. Bull. 1981, 29, 3238.
85. (d) Cassidy, F.; Moore, R. W.; Wootton, G.; Baggaley, K. H.; Geen, G. R.; Jennings, L. J. A.; Tyrrell, A. W. R. Tertahedron Lett. 1981, 22, 253.
86. (e) Stevens, R. V.; Vinogradoff, A. P. J. Org. Chem. 1985, 50, 4056.
87. (f) Skattebøl, L.; StenstrØm, Y. Acta Chem. Scand. B 1985, 39, 291.
88. (a) Laganis, E. D.; Chenard, B. L. Tetrahedron Lett. 1984, 25, 5831.
89. (b) Baldwin, J. E.; Adlington, R. M.; Mitchell, M. B. J. Chem. Soc., Chem. Commun. 1993, 1332.
90. (a) Olah, G. A.; Narang, S. C.; Balaram Gupta, B. G.; Malhotra, R. J. Org. Chem. 1979, 44, 1247.
91. (b) Lott, R. S.; Chauhan, V. S.; Stammer, C. H. J. Chem. Soc., Chem. Commun. 1979, 495.
92. (c) Ho, T.-L.; Olah, G. A. Angew. Chem., Int. Ed. Engl. 1976, 15, 774.
93. (d) Jung, M. E.; Lyster, M. A. J. Am. Chem. Soc. 1977, 99, 968.
94. (e) Monta, T.; Okamoto, Y.; Sakurai, H. J. Chem. Soc., Chem. Commun. 1978, 874.
95. (a) Vaughan, W. R.; Baumann, J. B. J. Org. Chem. 1962, 27, 739.
96. (b) Feutrill, G. I.; Mirrington, R. N. Aust. J. Chem. 1972, 25, 1731.
97. (c) Komblum, N.; Scott, A. J. Am. Chem. Soc. 1974, 96, 590.
98. (d) Bartlett, P. A.; Johnson, W. S. Tetrahedron Lett. 1970, 4459.
99. For a review of dealkylation methods, see: (e) McMurray, J. Org. React. 1976, 24, 187.
100. (a) Node, M.; Nishide, K.; Sai, M.; Fuji, K.; Fujita, E. J. Org. Chem. 1981, 46, 1991.
101. (b) Node, M.; Nishide, K.; Sai, M.; Fujita, E. Tetrahedron Lett. 1978, 5211.
102. (c) Williard, P. G.; Fryhle, C. B. Tetrahedron Lett. 1980, 27, 3731.
103. (a) Liu, H.-W.; Auchus, R.; Walsh, C. T. J. Am. Chem. Soc. 1984, 106, 5335.
104. (b) Gawronski, J. K.; Reddy, S. M.; Walborsky, H. M. J. Am. Chem. Soc. 1987, 109, 6726.
105. (a) Luche, J.-L.; Gemal, A. L. J. Chem. Soc., Chem. Commun. 1978, 976.
106. (b) Gemal, A. L.; Luche, J.-L. J. Org. Chem. 1979, 44, 4187.
107. For a review of transesterification, see: (c) Otera, J. Chem. Rev. 1993, 93, 1449.
108. Nelsen, S. F.; Gillespie, J. P. J. Org. Chem. 1975, 40, 2391.
109. An alternative method for the preparation of this compound has been reported: Neises, B.; Steglich, W. Org. Synth. 1985, 63, 183.
110. Patel, D. V.; VanMiddlesworth, F.; Donaubauer, J.; Gannett, P.; Sih, C. J. J. Am. Chem. Soc. 1986, 108, 4603.
111. Veibel, S.; Pedersen, C. Acta Chem. Scand. 1955, 9, 1674.
112. For alternative methods for the preparation of the acid chloride, see: (a) Oiwa, M.; Matsumoto, A. Jpn. Kokai Tokkyo Koho JP 62 45,561, 1987: Chem. Abstr. 1987, 107, 176634b. Several methods exist for the preparation of the monoisopropyl fumaric acid, as an example: (b) Zecher, W.; Merten, R. Eur. Pat. Appl. EP 69926 A1, 1983. (c) Gordinskii, B. Y.; Shimanskii, V. M.; Vishnyakova, R. S. Zh. Prikl. Kim. 1967, 40, 1881. (d) Ushakov, S. N.; Nikolaev, A. F.; Toroptseva, A. M.; Trizno, M. S. Zh. Prikl. Kim. 1959, 32, 667.
113. For alternative methods for the preparation of the acid chloride, see: (a) Oiwa, M.; Matsumoto, A. Jpn. Kokai Tokkyo Koho JP 62 45,561, 1987: Chem. Abstr. 1987, 107, 176634b. Several methods exist for the preparation of the monoisopropyl fumaric acid, as an example: (b) Zecher, W.; Merten, R. Eur. Pat. Appl. EP 69926 A1, 1983. (c) Gordinskii, B. Y.; Shimanskii, V. M.; Vishnyakova, R. S. Zh. Prikl. Kim. 1967, 40, 1881. (d) Ushakov, S. N.; Nikolaev, A. F.; Toroptseva, A. M.; Trizno, M. S. Zh. Prikl. Kim. 1959, 32, 667.
114. For alternative methods for the preparation of the acid chloride, see: (a) Oiwa, M.; Matsumoto, A. Jpn. Kokai Tokkyo Koho JP 62 45,561, 1987: Chem. Abstr. 1987, 107, 176634b. Several methods exist for the preparation of the monoisopropyl fumaric acid, as an example: (b) Zecher, W.; Merten, R. Eur. Pat. Appl. EP 69926 A1, 1983. (c) Gordinskii, B. Y.; Shimanskii, V. M.; Vishnyakova, R. S. Zh. Prikl. Kim. 1967, 40, 1881. (d) Ushakov, S. N.; Nikolaev, A. F.; Toroptseva, A. M.; Trizno, M. S. Zh. Prikl. Kim. 1959, 32, 667.
115. For alternative methods for the preparation of the acid chloride, see: (a) Oiwa, M.; Matsumoto, A. Jpn. Kokai Tokkyo Koho JP 62 45,561, 1987: Chem. Abstr. 1987, 107, 176634b. Several methods exist for the preparation of the monoisopropyl fumaric acid, as an example: (b) Zecher, W.; Merten, R. Eur. Pat. Appl. EP 69926 A1, 1983. (c) Gordinskii, B. Y.; Shimanskii, V. M.; Vishnyakova, R. S. Zh. Prikl. Kim. 1967, 40, 1881. (d) Ushakov, S. N.; Nikolaev, A. F.; Toroptseva, A. M.; Trizno, M. S. Zh. Prikl. Kim. 1959, 32, 667.
116. Review of the Mitsunobu reaction: Hughes, D. L. Org. React. 1992, 42, 335.
117. The production of a single anomer or a high anomeric ratio was important to achieve good yield in the subsequent reaction, as the minor component could never be isolated after workup (vide infra).
118. Dodge, J. A.; Trujillo, J. I.; Presnell, M. J. Org. Chem. 1994, 59, 234.
119. Mandal, A. K.; Soni, N. R.; Ratnam, K. R. Synthesis 1985, 274.
120. Nakajima, N.; Uoto, K.; Yonemitsu, O.; Hata, T. Chem. Pharm. Bull. 1991, 39, 64.
121. Denholm, A. A. Ph.D. Thesis, University of Glasgow, 1990. We gratefully acknowledge professor David J. Robins for the copies of this experimental procedure.
122. We are not aware of a report in the open literature discussing this phenomena, but considering the enormous numbers of papers in this field, a report could have been unintentionally missed.