Excellent chiral introduction by diene iron-tricarbonyl moiety. II: A formal synthesis of (+)- and (-)-frontalin using a diastereoselective 1,2-nucleophilic addition of organometallics into a (Z)-dienone Fe(CO)3 complex

Chemical and Pharmaceutical Bulletin

Volumn 44, Issue 5, 1996, Pages 940-947

  Takemoto, Yoshiji ^a   Takeuchi, Jun ^a   Morio, Ken Ichiro ^a   Nakamoto, Takahisa ^a   Iwata, Chuzo ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

1,2 nucleophilic addition; Formal synthesis; Frontalin; Olefin isomerization; Organometallic; Z dienone iron tricarbonyl complex

Indexed keywords

FRONTALIN; ORGANOMETALLIC COMPOUND;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ISOMERISM; STEREOCHEMISTRY;

EID: 0029897285     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.44.940     Document Type: Article

References (55)

1. Takemoto Y., Ueda S., Takeuchi J., Nakamoto T., Iwata C., Ohishi H., Sakaguchi K., Kusunoki M., Chem. Pharm. Bull., 43, 559-563 (1995).
2. Huryn D. M., "Comprehensive Organic Synthesis," Vol. 1, ed. by Trost B. M., Fleming I. E., Pergamon Press, Oxford, 1991, pp. 49-76.
3. a) Eliel E. L., M-Natschke S., J. Am. Chem. Soc., 106, 2937-2942 (1984);
4. b) Lynch J. E., Eliel E. L., ibid., 106, 2943-2948 (1984);
5. c) Frye S. V., Eliel E. L., J. Org. Chem., 50, 3402-3404 (1985);
6. d) Ohwa M., Eliel E. L., Chem. Lett., 1987, 41-44.
7. a) Mukaiyama T., Sakito Y., Asami M., Chem. Lett., 1978, 1253-1256;
8. b) Idem, ibid., 1979, 705-708;
9. c) Sakito Y., Mukaiyama T., ibid., 1979, 1027-1028;
10. d) Sakito Y., Tanaka S., Asami M., Mukaiyama T., ibid., 1980, 1223-1226.
11. a) Tamura Y., Kondo H., Annoura H., Takeuchi R., Fujioka H., Tetrahedron Lett., 27, 81-82 (1986);
12. b) Tamura Y., Ko T., Kondo H., Annoura H., Fuji M., Takeuchi R., Fujioka H., ibid., 27, 2117-2120 (1986);
13. c) Tamura Y., Annoura H., Yamamoto H., Kondo H., Kita Y., Fujioka H., ibid., 28, 5709-5712 (1987).
14. Fujisawa T., Ukaji Y., Yuki Gosei Kagaku Kyokaishi, 47, 186-199 (1989).
15. a) Utimoto K., Nakamura A., Matsubara S., J. Am. Chem. Soc., 112, 8189-8190 (1990);
16. b) Fujisawa T., Funabora M., Ukaji Y., Sato T., Chem. Lett., 1988, 59-62;
17. c) Fujisawa T., Takemura I., Ukaji Y., Tetrahedron Lett., 31, 5479-5462 (1990);
18. d) Ukaji Y., Yamamoto K., Fukui M., Fujisawa T., ibid., 32, 2919-2922 (1991).
19. a) Franck-Neumann M., "Organometallics in Organic Synthesis," ed. by de Meijere A., Dieck H. T., Springer-Verlag, Berlin, 1987, pp. 247-264;
20. b) Gree R., Synthesis, 1989, 341-355, references cited therein;
21. c) Pearson A. J., "Iron Compounds in Organic Synthesis," Academic Press, London, 1994, pp. 67-96;
22. d) Franck-Neumann M., Martina D., Heitz M-P., J. Organomet. Chem., 301, 61-77 (1986);
23. e) Roush W. R., Wada C. K., J. Am. Chem. Soc., 116, 2151-2152 (1994);
24. f) Takemoto Y., Ueda S., Takeuchi J., Nakamoto T., Iwata C., Tetrahedron Lett., 35, 8821-8824 (1994);
25. g) Takemoto Y., Ueda S., Takeuchi J., Nakamoto T., Iwata C., Ohishi H., Sakaguchi K., Kusunoki M., Chem. Pharm. Bull., 43, 559-563 (1995);
26. h) Takemoto Y., Yoshikawa N., Iwata C., J. Chem. Soc., Chem. Commun., 1995, 631-632.
27. Franck-Neumann M., Chemla P., Martina D., Synlett, 1990, 641-642.
28. The hydride reduction of a Z-dienone complex proceeds stereoselectively, giving rise to a secondary Z-dienol complex as a single product.: Franck-Neumann M., Abdali A., Colson P.-J., Sedrati M., Synlett, 1991, 331-334.
29. Frederiksen J. S., Graf R. E., Gresham D. G., Lillya C. P., J. Am. Chem. Soc., 101, 3863-3867 (1979).
30. A part of this work has been published in a preliminary communication: Takemoto Y., Takeuchi J., Iwata C., Tetrahedron Lett., 34, 6067-6068 (1993).
31. Compounds (1a and 3a) were reported in reference 13a); a) Graf R. E., Lillya C. P., J. Organomet. Chem., 122, 377-391 (1976);
32. b) Franck-Neumann M., Sedrati M., Mokhi M., New. J. Chem., 14, 471-480 (1990).
33. The stereochemistry of 4 was deduced from the result of a hydride reduction of the Z-dienone complex; see reference 10).
34. 2O, and TMSOTf gave rise to 1a as a sole product in 76%, 75%, and 67% yield, respectively.
35. Kinzer G. W., Fentimar A. F., Jr., Page T. F., Jr., Foltz R. L., Vite J. P., Pitman G. B., Nature (London), 221, 477-478 (1969).
36. a) Meister C., Scharf H. D., Liebigs Ann. Chem., 1983, 913-921;
37. b) Lee A. W. M., J. Chem. Soc., Chem. Commun., 1984, 578-579;
38. c) Johnston B. D., Oehlschlager A. C., Can. J. Chem., 62, 2148-2154 (1984);
39. d) Yadav J. S., Joshi B. V., Saharabudhe A. B., Synth. Commun., 15, 797-805 (1985);
40. e) Hosokawa T., Makabe Y., Shinohara T., Murahashi S. I., Chem. Lett., 1985, 1529-1530;
41. f) Chan T. H., Chen L. M., Wang D., Li L. H., Can. J. Chem., 71, 60-67 (1993).
42. a) Fuganti C., Grasselli P., Servi S., J. Chem. Soc., Perkin Trans. 1, 1983, 241-244;
43. b) Sato T., Maeno H., Noro T., Fujisawa T., Chem Lett., 1988, 1739-1742;
44. c) Ohta H., Kimura Y., Sugano Y., Sugai T., Tetrahedron, 45, 5469-5476 (1989);
45. d) Sugai T., Kakeya H., Ohta H., J. Org. Chem., 55, 4643-4647 (1990);
46. e) Ferraboschi P., Casati S., Grisenti P., Santaniello E., Tetrahedron: Asymmetry, 4, 9-12 (1993).
47. a) Whitesell J. K., Buchanan C. M., J. Org. Chem., 51, 5443-5445 (1986);
48. b) Fujisawa T., Takemura I., Ukaji Y., Tetrahedron Lett., 31, 5479-5482 (1990);
49. c) Mash E. A., Fryling J. A., J. Org. Chem., 56, 1094-1098 (1991);
50. d) Nemoto H., Yamada T., Ishibashi H., Takazawa J., Fukumoto K., Heterocycles, 32, 863-866 (1991);
51. e) Nemoto H., Yamada T., Ishibashi H., Fukumoto K., J. Chem. Soc., Perkin Trans. 1, 1991, 3149-3151.
52. Franck-Neumann M., Briswalter C., Chemla P., Martina D., Synlett, 1990, 637-640.
53. Wood N. F., Chang F. C., J. Org. Chem., 30, 2054-2055 (1965).
54. Franck-Neumann M., Heitz M. P., Martina D., Tetrahedron Lett., 24, 1615-1616 (1983).
55. Emerson G. F., Mahler J. E., Kochhar R., Pettit R., J. Org. Chem., 29, 3620-3624 (1964).