Stereoselective syntheses of (±)-komaroviquinone and (±)-faveline methyl ether through intramolecular Heck reaction

Journal of Organic Chemistry

Volumn 70, Issue 19, 2005, Pages 7694-7700

  Sengupta, Sujaya ^a   Drew, Michael G B ^b   Mukhopadhyay, Ranjan ^a   Achari, Basudeb ^a   Banerjee, Asish Kr ^a  

^a INDIAN INSTITUTE OF CHEMICAL BIOLOGY   (India)

^b UNIVERSITY OF READING   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; CHEMICAL BONDS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

DIMETHYL ETHER; INTERMOLECULAR HECK REACTION; STEREOSELECTIVE CONVERGENT ROUTES;

ETHERS;

10 HYDROXY 1,1 DIMETHYLOCTAHYDRODIBENZO[A,D]CYCLOHEPTEN 7 ONE DERIVATIVE; 4A HYDROXY 7 METHOXY 1,1 DIMETHYL 1,2,3,4,4A,5,11,11A OCTAHYDRODIBENZO[A,D]CYCLOHEPTEN 10 ONE; 4A HYDROXY 8 ISOPROPYL 6,7,9 TRIMETHOXY 1,1 DIMETHYL 1,2,3,4,4A,5,11,11A OCTAHYDRODIBENZO[A,D]CYCLOHEPTEN 10 ONE; ANTITRYPANOSOMAL AGENT; CNIDOSCOLUS PHYLLACANTHUS EXTRACT; COULTERONE; CYCLOCOULTERONE; CYCLOHEPTENE; DEOXOFAVELINE; FAVELINE; FAVELINE METHYL ETHER; KOMAROVIQUINONE; PLANT EXTRACT; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; DITERPENE; QUINONE DERIVATIVE;

ARTICLE; CNIDOSCOLUS PHYLLACANTHUS; DRUG ACTIVITY; DRUG SYNTHESIS; HECK REACTION; PLANT; STEREOCHEMISTRY; TRYPANOSOMA CRUZI; SYNTHESIS;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; DITERPENES; QUINONES;

EID: 24944588765     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051082i     Document Type: Article

References (51)

1. Endo, Y.; Ohta, Y.; Nozoe, S. Tetrahedron Lett. 1991, 32, 3083-3086.
2. (a) Yatagai, M.; Takahashi, T. Phytochemistry 1980, 19, 1149-1151.
3. (b) Hasegawa, S.; Hirose, Y.; Yatagai, M.; Takahashi, T. Chem. Lett. 1984, 1837-1838.
4. (c) Hasegawa, S.; Kojima, T.; Hirose, Y. Phytochemistry 1985, 24, 1545-1551.
5. (d) Kelecom, A. Tetrahedron 1983, 39, 3603-3609.
6. Frontana, B.; Cárdenas, J.; Rodríguez-Hahn, L. Phytochemistry 1994, 36, 739-741.
7. Uchiyama, N.; Kiuchi, F.; Ito, M.; Honda, G.; Takeda, Y.; Khodzhimatov, O. K.; Ashurmetov, O. A. J. Nat. Prod. 2003, 66, 128-131.
8. (a) Matsumoto, T.; Imai, S.; Yoshinari, T.; Matsuno, S. Bull. Chem. Soc. Jpn. 1986, 59, 3103-3108.
9. (b) Kametani, T.; Kondoh, H.; Tsubuki, M.; Honda, T. J. Chem. Soc., Perkin Trans. 1 1990, 5-10.
10. (c) Majetich, G.; Hicks, R.; Zhang, Y.; Tian, X.; Feltman, T. L.; Fang, J.; Duncan, S., Jr. J. Org. Chem. 1996, 61, 8169-8185.
11. (a) Ghosh, A. K.; Ray, C.; Ghatak, U. R. Tetrahedron Lett. 1992, 33, 655-658.
12. (b) Deb, S.; Bhattacharjee, G.; Ghatak, U. R. J. Chem. Soc., Perkin Trans. 1 1990, 1453-1458.
13. (a) Koft, E. R. Tetrahedron 1987, 43, 5775-5780.
14. (b) Majetich, G.; Zhang, Y.; Feltman, T. L.; Duncan, S., Jr. Tetrahedron Lett. 1993, 34, 445-448.
15. (a) Ghosh, A. K.; Ray, C.; Ghatak, U. R. Tetrahedron Lett. 1992, 33, 655-658.
16. (b) Ghosh, A. K.; Mukhopadhyay, C.; Ghatak, U. R. J. Chem. Soc., Perkin Trans. 1 1994, 327-332.
17. Banerjee, M.; Mukhopadhyay, R.; Achari, B.; Banerjee, A. Kr. Org. Lett. 2003, 5, 3931-3933.
18. Sengupta, S.; Mukhopadhyay, R.; Achari, B.; Banerjee, A. Kr. Tetrahedron Lett. 2005, 46, 1515-1519.
19. For examples of the intramolecular 7-exo Heck reaction, see the following articles and reviews and the references therein: (a) Gracias, V.; Moore, J. D.; Djuric, S. T. Tetrahedron Lett. 2004, 45, 417-420.
20. (b) Tietze, L. F.; Sommer, K. M.; Schneider, G.; Tapolcsányi, P.; Wõlfling, J.; Mûller, P.; Noltemeyer, M.; Terlau, H. Synlett 2003, 1494-1496.
21. (c) Santose, L. S.; Pilli, R. A. Synthesis 2002, 87-93.
22. (d) Caddick, S.; Kofie, W. Tetrahedron Lett. 2002, 43, 9347-9350.
23. (e) Link, J. T. Org. React. 2002, 60, 157-534.
24. (f) Tietze, L. F.; Ila, H.; Bell, H. P. Chem. Rev. 2004, 104, 3453-3516.
25. (g) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009-3066.
26. (h) Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945-2963.
27. Link, J. T. In The Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley, Sons: New York, 2002; Vol. 1, pp 1523-1560.
28. (j) Link, J. T.; Overman, L. E. In Metal Catalyzed Cross Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; pp 99-154.
29. (a) Abad, A.; Agulló, C.; Arnó, M.; Cuñat, A. C.; Meseguer, B.; Zaragozá, R. J. J. Org. Chem. 1998, 63, 5100-5106.
30. (b) Ashby, E. C.; Laemmle, J. T. Chem. Rev. 1975, 75, 521-546.
31. Fleifel, A. M. J. Org. Chem. 1960, 25, 1024-1025.
32. Chakraborti, A. K.; Basak, A.; Grover, V. J. Org. Chem. 1999, 64, 8014-8017.
33. Sishido, K.; Goto, K.; Miyoshi, S.; Takaishi, Y.; Shibuya, M. J. Org. Chem. 1994, 59, 406-414.
34. Tori, M.; Hamaguchi, T.; Sagawa, K.; Sono, M.; Asakawa, Y. J. Org. Chem. 1996, 61, 5362-5370.
35. Burnell, R. H.; Caron, S. Can. J. Chem. 1992, 1446-1454 [for an alternative method of preparation of 17].
36. Pal, S.; Mukhopadhyay, J. K.; Ghatak, U. R. J. Org. Chem. 1994, 59, 2687-2694.
37. Cairns, P. M.; Howes, C.; Jenkins, P. R. J. Chem. Soc., Perkin Trans. 1 1990, 627-632.
38. Begbie, A. L.; Golding, B. T. J. Chem. Soc., Perkin Trans. 1 1972, 602-605.
39. The ORTEP diagrams of 5a and 24b are given in the Supporting Information.
40. Carreno, M. C.; Ruano, J. L. G.; Sanz, G.; Toledo, M. A.; Urbano, A. J. Org. Chem. 1995, 60, 5328-5331.
41. Tanino, K.; Onuki, K.; Asano, K.; Miyashita, M.; Nakamura, T.; Takahashi, Y.; Kuwajima, I. J. Am. Chem. Soc. 2003, 125, 1498-1500.
42. (a) Schlosser, M. Eur. J. Org. Chem. 2001, 3975-3984.
43. (b) Westheimer, F. H. In Steric Effects in Organic Chemistry; Newman, M. S., Ed.; Wiley: New York, 1956; pp 523-555.
44. (a) Clive, D. L. J.; Yu, M.; Sannigrahi, M. J. Org. Chem. 2004, 69, 4116-4125.
45. (b) Iguchi, M.; Nishiyama, A.; Etoh, H.; Okamoto, K.; Yamamura, S.; Kato, Y. Chem. Pharm. Bull. 1986, 34, 4910-4915.
46. Ma, S.; Ni, B. J. Org. Chem. 2002, 67, 8280-8288.
47. Clive, D. L. J.; Wang, J. J. Org. Chem. 2004, 69, 2773-2784.
48. 3 solution (where the presence of traces of acid is not unexpected) and after a week's time, the minor form appeared to have become the major one.
49. Snyder, C. D.; Rapoport, H. J. Am. Chem. Soc. 1972, 94, 227-231.
50. Allen, W. S.; Bernstein, S. J. Am. Chem. Soc. 1955, 77, 1028-1032.
51. Ho, T. L.; Chen, C. K. Tetrahedron 1995, 51, 5819-5824.