Diels—Alder Reactions of Heterocyclic Azadienes: Total Synthesis of PDE I, PDE II, and PDE I Dimer Methyl Ester

Journal of the American Chemical Society

Volumn 109, Issue 9, 1987, Pages 2717-2727

  Boger, Dale L ^a   Coleman, Robert S ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845283430     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00243a027     Document Type: Article

References (45)

1. Hanka, L. J.; Dietz, A,; Gerpheide, S. A.; Kuentzel, S. L.; Martin, D. G. J. Antibiot. 1978, 31, 1211. Martin, D. G.; Biles, C.; Gerpheide, S. A.; Hanka, L. J.; Krueger, W. C.; McGovren, J. P.; Mizsak, S. A.; Neil, G. L.; Stewart, J. C.; Visser, J. J. Antibiot. 1981, 34, 1119. The antibiotic ra-chelmycin, isolated from Streptomyces strain C-329, has been shown to be identical with CC-1065: Nettleton, D. E.; Bush, J. A.; Bradner, W. T. U. S. Patent 4 301 248; Chem. Abstr. 1982, 96, 33362e. Review of the chemistry, biosynthesis, synthesis, pharmacology, and toxicology of CC-1065: Reynolds, V. L.; McGovren, J. P.; Hurley, L. H. J. Antibiot. 1986, 31, 319. Review of the covalent binding of CC-1065 in B-DNA minor groove: Hurley, L. H.; Needham-VanDevanter. D. R. Acc. Chem. Res. 1986, 19, 230.
2. Martin, D. G.; Chidester, C. G.; Duchamp, D. J.; Mizsak, S. A. J. Antibiot. 1980 33, 902. (b) Chidester, C. G.; Krueger, W. C.; Mizsak, S. A.; Duchamp, D. J.; Martin, D. G. J. Am. Chem. Soc. 1981, 103. 7629.
3. Bhuyan, B. K.; Newell, K. A.; Crampton, S. L.; vonHoff, D. D. Cancer Res. 1982, 42, 3532.
4. Swenson, D. H.; Li, L. H.; Hurley, L. H.; Rokem, J. S.; Petzold, G. L.; Dayton, B. D.; Wallace, T. L.; Lin, A. H.; Krueger, W. C. Cancer Res. 1982, 42, 2821. Li, L. H.; Swenson, D. H.; Schpok, S. L. F.; Kuentzel, S. L.; Dayton, B. D.; Krueger, W. C. Cancer Res. 1982, 42, 999. Reynolds, V. L.; Molineux, I. J.; Kaplan, D. J.; Swenson, D. H.; Hurley, L. H. Biochemistry 1985, 24, 6228.
5. Hurley, L. H.; Reynolds, V. L.; Swenson, D. H.; Petzold, G. L.; Scahill, T. A. Science (Washington, DC) 1984, 226, 843. Needham-VanDevanter, D. R.; Hurley, L. H.; Reynolds, V. L.; Theriault, N. Y.; Krueger, W. C.; Wierenga, W. Nucleic Acids Res. 1984, 12, 6159.
6. Warpehoski, M. A. Tetrahedron Lett. 1986, 27, 4103. Warpehoski, M. A.; Kelly, R. C.; McGovren, J. P.; Wierenga, W. Cancer Res. 1985 26, 870. Lee, C. S. ; Hurley, L. H. Cancer Res. 1986, 27, 962. Wierenga, W.; Bhuyan, B. K.; Kelly, R. C.; Krueger, W. C.; Li, L. H.; McGovren, J. P.; Swenson, D. H.; Warpehoski, M. A. Adv. Enzyme Regul. 1986, 25, 141.
7. McGovren, J. P.; Clarke, G. L.; Pratt, E. A.; DeKoning, T. F. J. Antibiot. 1984, 37, 63.
8. Warpehoski, M. A.; Bradford, S. V. Tetrahedron Lett. 1986, 27, 2735. Kelly, R. C.; Warpehoski, M. A.; Wierenga, W. Eur. Patent Application EP 154445 (U. S. Patent Application 581 836); Chem. Abstr. 1986, 104, 148641w.
9. Jones, R. J.; Cava, M. P. J. Chem. Soc., Chem. Commun. 1986, 826. Rawal, V. H.; Jones, R. J.; Cava, M. P. J. Org. Chem. 1987, 52, 19.
10. Enomoto, Y.; Furutani, Y.; Naganawa, H.; Hamada, M.; Takeuchi, T.; Umezawa, H. Agric. Biol. Chem. 1978, 42, 1331.
11. Nakamura, H.; Enomoto, Y.; Takeuchi, T.; Umezawa, H.; Iitaka, Y. Agric. Biol. Chem. 1978, 42, 1337.
12. Komoto, N.; Enomoto, Y.; Tanaka, Y.; Nitanai, K.; Umezawa, H. Agric. Biol. Chem. 1979, 43, 559 (PDE I). (b) Komoto, N.; Enomoto, Y.; Miyagaki, M.; Tanaka, Y.; Nitanai, K.; Umezawa, H. Agric. Biol. Chem. 1979, 43, 555 (PDE II).
13. Total syntheses of PDE I and PDE II: (a) Bolton, R. E.; Moody, C. J.; Rees, C. W.; Tojo, G. J. Chem. Soc., Chem. Commun. 1985, 1775 (PDE I and II). (b) Rawal, V. H.; Cava, M. P. J. Am. Chem. Soc. 1986, 108, 2110 (PDE I and II methyl esters), (c) Boger, D. L.; Coleman, R. S. J. Org. Chem. 1986, 51, 3250 (PDE II methyl ester), (d) Carter, P.; Fitzjohn, S.; Magnus, P. J. Chem. Soc., Chem. Commun. 1986, 1162. Carter, P.; Fitzjohn, S.; Halazy. S.; Magnus, P. J. Am. Chem. Soc., in press (PDE I and II).
14. Synthetic studies on CC-1065: (a) Preparation of the left-hand segment of CC-1065: Wierenga, W. J. Am. Chem. Soc. 1981, 103, 5621. Magnus, P.; Gallagher, T. J. Chem. Soc., Chem. Commun. 1984, 389. Magnus, P.; Gallagher, T.; Schultz, J.; Or, Y. S. ; Ananthanarayan, T. P. J. Am. Chem. Soc., in press. Kraus, G. A.; Yue, S.; Sy, J. J. Org. Chem. 1985, 50, 284. Moody, C. J.; Pass, M.; Rees, C. W.; Tajo G. J. Chem. Soc., Chem. Commun. 1986, 1062. (b) Studies on the preparation of the monomer units of CC-1065: Kraus, G. A.; Yue, S. J. Chem. Soc., Chem. Commun. 1983, 1198. Rawal, V. H.; Cava, M. P. J. Chem. Soc., Chem. Commun. 1984, 1526. Magnus, P.; Or, Y. S. Mol. Phys. 1983, 26. Halazy, S.; Magnus, P. Tetrahedron Lett. 1984, 25, 1421. Magnus, P.; Halazy, S. Mol. Phys. 1985, 26, 2985. Sundberg, R. J.; Nishiguchi, T. Mol. Phys. 1983, 24, 4773. Sundberg, R. J.; Pearce, B. C. J. Org. Chem. 1985, 50, 425. Sundberg, R. J.; Baxter, E. W.,Tetrahedron Lett. 1986, 27, 2687. Bryson, T. A.; Roth, G. A.; Jing-hua, L. Mol. Phys. 1986, 27, 3685. Bryson, T. A.; Roth, G. A. Mol. Phys. 1986, 27, 3689. See also ref 18 and 57. (c)
15. Review: Boger, D. L. Tetrahedron 1983, 39, 2869. Boger, D. L. Chem. Rev. 1986, 86, 781.
16. For a related strategy of 1,2,4,5-tetrazine → 1,2-diazine → pyrrole conversion, see: Boger, D. L.; Coleman, R. S.; Panek, J. S.; Yohannes, D. J. Org. Chem. 1984, 49 4405.
17. Boger, D. L.; Coleman, R. S. J. Org. Chem. 1984, 49, 2240.
18. Boger, D. L.; Coleman, R. S.; Panek, J. S.; Huber, F. X.; Sauer, J. J. Org. Chem. 1985, 50, 5377. (b) Spencer, G. H., Jr.; Cross, P. C.; Wiberg, K. B. J. Chem. Phys. 1961, 35, 1939. Sauer, J.; Mielert, A.; Lang, D.; Peter, D. Chem. Ber. 1965, 98, 1435. Curtius, T.; Darapsky, A.; Miiller, E. Chem. Ber. 1906, 39, 3410; 1907, 40, 84; 1908, 41, 3161 and earlier references cited therein.
19. intramolecular alkene 1,2-diazine Diels-Alder reactions, see: Jojima, T.; Takeshiba, H.; Konotsune, T. Chem. Pharm. Bull. 1972, 20, 2191. Jojima, T.; Takeshiba, H.; Konoto, T. Mol. Phys. 1976, 24, 1581, 1588; 1980, 28, 198. For a summary of the Diels-Alder reactions of 1,2-diazines, see ref 16.
20. Hemetsberger, H.; Knittle, D. Monatsh. Chem. 1972, 103, 194. MacKenzie, A. R.; Moody, C. J.; Rees, C. W. J. Chem. Soc., Chem. Commun. 1983, 1372. See also: Isomura, K.; Kobayashi, S.; Taniguchi, H. Tetrahedron Lett. 1968 3499.
21. Boger, D. L.; Coleman, R. S. J. Org. Chem. 1986, 51, 5436.
22. Banville, J.; Brassard, P. J. Chem. Soc., Perkin Trans. 1 1976, 1852.
23. Thomason, S. C.; Kubler, D. G. J. Chem. Educ. 1968, 45, 546.
24. Yates, P.; Anderson. C. D. J. Am. Chem. Soc. 1963, 85, 2937.
25. Adjangba, M. S.; Barnes, E. P. D.; Ikonne, J. V. Ghana J. Sci. 1969, 9, 91.
26. Harland, P. A.; Hodge, P. Synthesis 1983, 419.
27. Bonjouklian, R.; Ganem, B. Tetrahedron Lett. 1977, 2835. Edwards, O. E.; Ho, P. T. Can. J. Chem. 1977, 55, 371. Fischer, H. O. L.; Dangschat, G. Chem. Ber. 1932, 65, 1009.
28. Ninomiya, K.; Shioiri, T.; Yamada, S. Tetrahedron 1974 30, 2151. Ninomiya, K.; Shiorii, T.; Yamada, S. J. Am. Chem. Soc. 1972, 94, 6203.
29. Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190.
30. Radlick, P.; Brown, L. R. Synthesis 1974, 290.
31. Mitsunobu, O. Synthesis 1981, 1. Mitsunobu, O.; Wada, M.; Sano, T. J. Am. Chem. Soc. 1972, 94, 679.
32. Gassman, P. G.; Hodgson, P. K. G.; Balchunis, R. J. J. Am. Chem. Soc. 1976, 98, 1275. Gassman, P. G.; Schenk, W. N. J. Org. Chem. 1977, 42, 918.
33. Forster, M. O.; Fierz, H. E. J. Chem. Soc. 1908, 93. 72.
34. Hassner, A.; Wiegand, N. H.; Gottlieb, H. E. J. Org. Chem. 1986, 51, 3176. Knittle, D. Synthesis 1985, 186. Hickey, D. M. B.; Moody, C. J.; Rees, C. W. J. Chem. Soc., Chem. Commun. 1982, 1419.
35. Imamoto, T.; Sugiura, Y.; Takiyama, N. Tetrahedron Lett. 1984, 25, 4233.
36. Trifluoroperacetic acid: Emmons, W. D.; Lucas, G. B. J. Am. Chem, Soc. 1955, 77, 2287. Wetter, H. Helv. Chim. Acta 1981, 64, 761.
37. 3,5-Dinitroperbenzoic acid: Rastetter, W. H.; Richard, T. J.; Lewis, M. D. J. Org. Chem. 1978, 43, 3163.
38. Permonophosphoric acid: Ogata, Y.; Tomizawa, K.; Ikeda, T. J. Org. Chem. 1978, 43, 2417.
39. o-Alkoxypercarbonic acids: Tsunokawa, Y.; Iwasaki S.; Okuda, S. Tetrahedron Lett. 1982, 23, 2113; Chem. Pharm. Bull. 1983, 31, 4578.
40. Acidic hydrogen peroxide: Matsumoto, M.; Kobayashi, H.; Hotta, Y. J. Org. Chem. 1984, 49, 4740.
41. Anderson, G. H.; Smith, J. G. Can. J. Chem. 1968, 46, 1553, 1561. (b) Kharasch, M. S.; Fono, A.; Nudenberg, W.; Poshkus, A. C. J. Org. Chem. 1950, 15, 775. (c) Deno, N. C.; Billups, W. E.; Kramer, K. E.; Lastomirsky, R. R. J. Org. Chem. 1970, 35, 3080. (d) Hawkins, E. G. E. Organic Peroxides; Van Nostrand: New York, 1961. (e) Davies, A. G. Organic Peroxides; Butterworths: London, 1961. (f) Lee, J. B.; Uff, B. C. Q. Rev., Chem. Soc. 1967, 21, 449. (g) For application of a hydroperoxide rearrangement in the total synthesis of triumferol, see: Kusumi, T.; Chang, C. C.; Wheeler, M.; Kubo, I.; Nakanishi, K.; Naoki, H. Tetrahedron Lett. 1981, 22, 3451. (h) For application of a hydroperoxide rearrangement in the synthesis of 4-hydroxypyrazoles, see: Albrand, M.; Gelin, S. Synthesis 1983, 1030.
42. McClure, J. D.; Williams, P. H. J. Org. Chem. 1962, 27, 24.
43. Diago-Meseguer, J.; Palomo-Coll, A. L.; Fernandez-Lizarbe, J. R.; Zugaza-Bilbao, A. Z. Synthesis 1980. 547.
44. Dhaon M. K.; Olsen, R. K.; Ramasamy, K. J. Org. Chem. 1982, 47, 1962.
45. Comparison was based on direct comparison of NMR (Me2SO-46, 200 MHz) and IR spectra of synthetic PDE I dimer methyl ester and a sample of PDE I dimer methyl ester derived from natural CC-1065 (Martin, D. G.; Mizsak, S. A.; Krueger, W. C. J. Antibiot. 1985, 38, 746) and kindly supplied by the Upjohn Company.