Shortcut syntheses of naturally occurring 5-alkylresorcinols with DNA-cleaving properties

Journal of Organic Chemistry

Volumn 62, Issue 8, 1997, Pages 2332-2336

  Furstner A ^a   Seidel, G ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ANACARDIC ACID; GINKGOLIC ACID DERIVATIVE; RESORCINOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS;

EID: 0030983374     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962423i     Document Type: Article

References (36)

1. Review: Tyman, J. H. P. Chem. Soc. Rev. 1979, 499-537.
2. (a) Lytollis, W.; Scannell, R. T.; An, H.; Murty, V. S.; Reddy, K. S.; Barr, J. R.; Hecht, S. M. J. Am. Chem. Soc. 1995, 117, 12683-12690.
3. (b) Singh, U. S.; Scannell, R. T.; An, H.; Carter, B. J.; Hecht, S. M. J. Am. Chem. Soc. 1995, 117, 12691-12699.
4. (c) Scannell, R. T.; Barr, J. R.; Murty, V. S.; Keddy, K. S.; Hecht, S. M. J. Am. Chem. Soc. 1988, 110, 3650-3651.
5. This metal-assisted scenario is reminiscent of the mode of action of metallobleomycins, although the elementary steps of oxygen transfer to the DNA may be different. For reviews see i.a.: (a) Hecht, S. M. Pure Appl. Chem. 1989, 61, 577-580. (b) Sugiyama, H.; Ehrenfeld, G. M.; Shipley, J. B.; Kilkuskie, R. E.; Chang, L.-H.; Hecht, S. M. J. Nat. Prod. 1985, 48, 869-877. (c) Stubbe, J.; Kozarich, J. W. Chem. Rev. 1987, 87, 1107-1136.
6. This metal-assisted scenario is reminiscent of the mode of action of metallobleomycins, although the elementary steps of oxygen transfer to the DNA may be different. For reviews see i.a.: (a) Hecht, S. M. Pure Appl. Chem. 1989, 61, 577-580. (b) Sugiyama, H.; Ehrenfeld, G. M.; Shipley, J. B.; Kilkuskie, R. E.; Chang, L.-H.; Hecht, S. M. J. Nat. Prod. 1985, 48, 869-877. (c) Stubbe, J.; Kozarich, J. W. Chem. Rev. 1987, 87, 1107-1136.
7. This metal-assisted scenario is reminiscent of the mode of action of metallobleomycins, although the elementary steps of oxygen transfer to the DNA may be different. For reviews see i.a.: (a) Hecht, S. M. Pure Appl. Chem. 1989, 61, 577-580. (b) Sugiyama, H.; Ehrenfeld, G. M.; Shipley, J. B.; Kilkuskie, R. E.; Chang, L.-H.; Hecht, S. M. J. Nat. Prod. 1985, 48, 869-877. (c) Stubbe, J.; Kozarich, J. W. Chem. Rev. 1987, 87, 1107-1136.
8. Wasser, C.; Silva, F.; Rodriguez, E. Experientia 1990, 46, 500-502.
9. (a) Arisawa, M.; Ohmura, K.; Kobayashi, A.; Morita, N. Chem. Pharm. Bull. 1989, 37, 2431-2434.
10. (b) Itokawa, H.; Totsuka, N.; Nakahara, K.; Takeya, K.; Lepoittevin, J.-P.; Asakawa, Y. Chem. Pharm. Bull. 1987, 35, 3016-3020.
11. See also: (a) Baylis, C. J.; Odle, S. W. D.; Tyman, J. H. P. J. Chem. Soc., Perkin Trans. 1 1981, 132-141. (b) Durrani, A. A.; Tyman, J. H. P. J. Chem. Soc., Perkin Trans. 1 1980, 1658-1666. (c) Alonso, E.; Ramon, D. J.; Yus, M. J. Org. Chem. 1997, 62, 417-421.
12. See also: (a) Baylis, C. J.; Odle, S. W. D.; Tyman, J. H. P. J. Chem. Soc., Perkin Trans. 1 1981, 132-141. (b) Durrani, A. A.; Tyman, J. H. P. J. Chem. Soc., Perkin Trans. 1 1980, 1658-1666. (c) Alonso, E.; Ramon, D. J.; Yus, M. J. Org. Chem. 1997, 62, 417-421.
13. See also: (a) Baylis, C. J.; Odle, S. W. D.; Tyman, J. H. P. J. Chem. Soc., Perkin Trans. 1 1981, 132-141. (b) Durrani, A. A.; Tyman, J. H. P. J. Chem. Soc., Perkin Trans. 1 1980, 1658-1666. (c) Alonso, E.; Ramon, D. J.; Yus, M. J. Org. Chem. 1997, 62, 417-421.
14. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
15. (b) Miyaura, N.; Ishiyama, T.; Sasaki, H.; Ishikawa, M.; Satoh, M.; Suzuki, A. J. Am. Chem. Soc. 1989, 111, 314-321.
16. (c) Oh-e, T.; Miyaura, N.; Suzuki, A. J. Org. Chem. 1993, 58, 2201-2208.
17. For recent methodological advancements in Suzuki reactions and for applications to the synthesis of physiologically active natural products from our laboratory see: (a) Fürstner, A.; Seidel, G. Tetrahedron 1995, 51, 11165-11176. (b) Fürstner, A.; Konetzki, I. Tetrahedron 1996, 52, 15071-15078. (c) Fürstner, A.; Nikolakis, K. Liebigs Ann. 1996, 2107-2113. (d) Fürstner, A.; Seidel, G.; Gabor, B.; Kopiske, C.; Krüger, C.; Mynott, R. Tetrahedron 1995, 51, 8875-8888.
18. For recent methodological advancements in Suzuki reactions and for applications to the synthesis of physiologically active natural products from our laboratory see: (a) Fürstner, A.; Seidel, G. Tetrahedron 1995, 51, 11165-11176. (b) Fürstner, A.; Konetzki, I. Tetrahedron 1996, 52, 15071-15078. (c) Fürstner, A.; Nikolakis, K. Liebigs Ann. 1996, 2107-2113. (d) Fürstner, A.; Seidel, G.; Gabor, B.; Kopiske, C.; Krüger, C.; Mynott, R. Tetrahedron 1995, 51, 8875-8888.
19. For recent methodological advancements in Suzuki reactions and for applications to the synthesis of physiologically active natural products from our laboratory see: (a) Fürstner, A.; Seidel, G. Tetrahedron 1995, 51, 11165-11176. (b) Fürstner, A.; Konetzki, I. Tetrahedron 1996, 52, 15071-15078. (c) Fürstner, A.; Nikolakis, K. Liebigs Ann. 1996, 2107-2113. (d) Fürstner, A.; Seidel, G.; Gabor, B.; Kopiske, C.; Krüger, C.; Mynott, R. Tetrahedron 1995, 51, 8875-8888.
20. For recent methodological advancements in Suzuki reactions and for applications to the synthesis of physiologically active natural products from our laboratory see: (a) Fürstner, A.; Seidel, G. Tetrahedron 1995, 51, 11165-11176. (b) Fürstner, A.; Konetzki, I. Tetrahedron 1996, 52, 15071-15078. (c) Fürstner, A.; Nikolakis, K. Liebigs Ann. 1996, 2107-2113. (d) Fürstner, A.; Seidel, G.; Gabor, B.; Kopiske, C.; Krüger, C.; Mynott, R. Tetrahedron 1995, 51, 8875-8888.
21. Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158-163.
22. Köster, R.; Seidel, G. In Organometallic Syntheses; King, R. B., Eisch, J. J., Eds.; Elsevier; Amsterdam, 1988; Vol. 4, pp 440-442.
23. Review: Marvell, E. N.; Li, T. Synthesis 1973, 457-468.
24. (a) Brown, H. G.; Wang, K. K. J. Org. Chem. 1986, 51, 4514-4517.
25. (b) Brown, H. C.; Scouten, C. G.; Liotta, R. J. Am. Chem. Soc. 1979, 101, 96-99.
26. (a) Prepared from n-BuLi and acetylene according to: Brandsma, L. Preparative Acetylenic Chemistry, 2nd ed.; Elsevier: Amsterdam, 1988; pp 23-24.
27. (b) For an alternative synthesis from n-BuLi and trichloroethylene see: Sekiguchi, A.; Ichinohe, M.; Kabuto, C.; Sakurai, H. Bull. Chem. Soc. Jpn. 1995, 68, 2981-2988. Dilithioacetylene prepared according to this latter procedure on alkylation with 10 gave, however, a somewhat lower yield of dienyne 11.
28. (a) For an alternative approach to anacardic acid and related salicylic acid derivatives and for a compilation of the literature see: Zehnter, R.; Gerlach H. Liebigs Ann. 1995, 2209-2220.
29. (b) For a report on the prostaglandin synthetase inhibitory activity of this compound see: Kubo, I.; Kim, M.; Naya, K.; Komatsu, S.; Yamagiwa, Y.; Ohashi, K.; Sakamoto, Y.; Hirakawa, S.; Kamikawa, T. Chem. Lett. 1987, 1101-1104.
30. For a review on ginkgolic acid see ref 1; it is also the major antitumor principle of the chloroform extracts of Ginkgo biloba, cf. ref 5b; for structure elucidation see: Morimoto, H.; Kawamatsu, Y.; Sugihara, H. Chem. Pharm. Bull. 1968, 16, 2282-2286.
31. Shan, R.; Anke, H.; Nielsen, M.; Sterner, O.; Witt, M. R. Nat. Prod. Lett. 1994, 4, 171-178.
32. For leading references on the design of artificial sequence specific DNA binding/cleaving agents see i.a.: (a) Dervan, P. B. Science 1986, 232, 464-471. (b) Barton, J. K. Science 1986, 233, 727-734. (c) Sigman, D. S. Acc. Chem. Res. 1986, 19, 180-186. (d) Chu, B. C. F.; Orgel, L. E. Proc. Nat. Acad. Sci. U.S.A. 1985, 82, 963-967 and lit cit.
33. For leading references on the design of artificial sequence specific DNA binding/cleaving agents see i.a.: (a) Dervan, P. B. Science 1986, 232, 464-471. (b) Barton, J. K. Science 1986, 233, 727-734. (c) Sigman, D. S. Acc. Chem. Res. 1986, 19, 180-186. (d) Chu, B. C. F.; Orgel, L. E. Proc. Nat. Acad. Sci. U.S.A. 1985, 82, 963-967 and lit cit.
34. For leading references on the design of artificial sequence specific DNA binding/cleaving agents see i.a.: (a) Dervan, P. B. Science 1986, 232, 464-471. (b) Barton, J. K. Science 1986, 233, 727-734. (c) Sigman, D. S. Acc. Chem. Res. 1986, 19, 180-186. (d) Chu, B. C. F.; Orgel, L. E. Proc. Nat. Acad. Sci. U.S.A. 1985, 82, 963-967 and lit cit.
35. For leading references on the design of artificial sequence specific DNA binding/cleaving agents see i.a.: (a) Dervan, P. B. Science 1986, 232, 464-471. (b) Barton, J. K. Science 1986, 233, 727-734. (c) Sigman, D. S. Acc. Chem. Res. 1986, 19, 180-186. (d) Chu, B. C. F.; Orgel, L. E. Proc. Nat. Acad. Sci. U.S.A. 1985, 82, 963-967 and lit cit.
36. For a convenient large-scale preparation see: Binger, P.; Köster, R. Inorg. Synth. 1974, 15, 147-149.