none 10.3987/COM-00-9008 CLOCKSS Archive CLOCKSS Archive 5187 36410299 73640 20090303102313 10.13030 2024-06-24T20:31:01Z 2009-03-03T01:24:22Z 31 HETEROCYCLES HETEROCYCLES 0385-5414 HTCYAM 2000 53 10 Minoru Ishikura Katsuaki Imaizumi Nobuya Katagiri 2000 2201 COM-00-9008 10.3987/COM-00-9008 20090303102313 https://triggered.stanford.clockss.org/ServeContent?doi=10.3987%2Fcom-00-9008 https://triggered.edinburgh.clockss.org/ServeContent?doi=10.3987%2Fcom-00-9008 10.1039/c39850000047 1. Y. C. Kong, K. F. Cheng, R. C. Cambie, and P.G. Waterman, J. Chem. Soc., Chem. Commun., 1985,47. 10.1159/000007257 2. a) T. W. Leung, G. Cheng, C. H. Chui, S. K. Ho, F. Y. Lau, J. K. Tjong, T. C. Poon, J. C. Tang, W. C. Tse, K. F. Cheng, and K. C. Kong, Chemotherapy, 2000, 46, 62. b) D. C. C. Wong, W. P. Fong, S. S. Lee, Y. C. Kong, K. F. Cheng, and G. Stone, Eur. J. Pharmacol., 1998, 362, 87. (c) P. C. Ng, D. D. Ho, K. H. Ng, Y. C. Kong, K. F. Cheng, and G. Stone, Eur. J. Pharmacol., 1994, 264, 1. d) K. F. Cheng, T. T. Wong, K. P. Chan, and Y. C. Kong, Eur. J. Med. Chem., 1992, 27, 121. e) D. D. Ho, C. P. Lau, K. H. Ng, Y. C. Kong, K. C. Kong, K. F. Cheng, and K. P. Chan, Eur. J. Pharmacol., 1991, 205, 209. f) M. Hammarstrom, L. Venemalm, J. Bergman, and P. Eneroth, Am. J. Clin. Med., 1990, 18, 1. g) Y. C. Kong, K. H. Ng, K. H. Wat, A. Wong, I. F. Saxena, K. F. Cheng, P. P. But, and H. T. Chang, Planta Med., 1985, 44, 304. h) F. illequin, M. Koch, M. Bert, and T. Sevenet, J. Nat. Prod., 1979, 42, 92. 3. a) J. Sapi and G. Massiot, “ The Chemistry of Heterocyclic Compounds: Bisindole Alkaloids,” Supplement to Vol. 25, part 4, ed. by J. E. Saxton, John Wiley & Sons, Ltd., Chichester, 1994, pp. 625-632. b) J. H. Sheu, C. A. Chen, and B. H. Chen, Chem. Commun., 1999, 203 c) J. H. Sheu, Y. K. Chen, H. F. Chung, S. F. Lin, and P. J. Sung, J. Chem. Soc., Perkin Trans. 1, 1998, 1959. d) K. F. Chen, M. K. Cheung, and Y. C. Kong, Aust. J. Chem., 1997, 50, 349. e) K. F. Cheng, M. K. Cheng, and Y. C. Kong, Aust. J. Chem., 1997, 50, 349. f) J. H. Sheu, Y. K. Chen, H. F. Chung, P. J. Sung, and S. F. Lin, Heterocycles, 1996, 43, 1751. g) K. F. Cheng and M. K. Cheung, J. Chem. Soc., Perkin Trans. 1, 1996,1213. h) G. A. Gao and K. F. Cheng, Synth. Commun., 1996, 26, 1525. i) V. Lee, M. K. Cheung, W. T. Wong, and K. F. Cheng, Tetrahedron, 1996, 28, 9455. j) J. H. Sheu, Y. K. Chen, H. F. Chung, P. J. Sung, and S. F. Lin, Heterocycles, 1996, 43, 1751. k) A. R. Katritzky, G. Zhang, L. Xie, and I. Hiviriga, J. Org. Chem., 1996, 61, 7558. l) C. A. Harrison, R. Leineweber, C. J. Moody, and J. M. J. Williams, J. Chem. Soc., Perkin Trans. 1, 1995, 1127. m) C. A. Harrison, P. M. Jackson, C. J. Moody, and J. M. J. Williams, J. Chem. Soc., Perkin Trans. 1, 1995, 1131. n) J. Bergman and L. Venemalm, Pure Appl. Chem., 1994, 66, 2331. o) K. F. Cheng, G. A. Gao, Y. W. Yu, and Y. C. Kong, Synth. Commun., 1994, 24, 65. p) J. H. Sheu, Y. K. Chen, and Y. L. V. Hong, J. Org. Chem., 1993, 58, 5784. q) J. Bergman and L. Venemalm, Tetrahedron, 1992, 48, 759. r) J. H. Sheu, Y. K. Chen, and Y. L. V. Hong, Tetrahedron Lett., 1991, 32, 1045. s) J. P. Kutney, F. J. Lopez, S. P. Huang, H. Kurobe, R. Flogaus, K. Piotrowska, and S. J. Rettig, Can. J. Chem., 1991, 69, 949. t) J. Bergman and L. Venemalm, Tetrahedtron, 1990, 46, 6067. u) J. P. Kutney, F. J. Lopez, S. P. Huang, and H. Kurobe, Heterocycles,1989, 28, 565. v) J. Bergman and L. Venemalm, Tetrahedron Lett., 1988, 29, 2993. w) K. F. Cheng, Y. C. Kong, and T. Y. Chan, J. Chem. Soc., Chem. Commun., 1985, 48. 10.1016/S0040-4020(99)01016-9 4. a) M. Ishikura, A. Hino, T. Yaginuma, I. Agata, and N. Katagiri, Tetrahedron, 2000, 56, 193. b) M. Ishikura and I. Agata, Recent Res. Devel. in Organic Chem., 1997, 1, 145. c) M. Ishikura, Yuki Gosei Kagaku Kyokaishi, 1995, 53, 308. 5. M. Ishikura and M. Terashima, J. Org. Chem., 1994, 59, 2634. 10.3987/COM-99-8822 6. a) M. Ishikura, Heterocycles, 1995, 41, 1385. b) M. Ishikura, K. Imaizumi, and N. Katagiri, Heterocycles, 2000, 53, 553. 10.1016/S0040-4039(00)60957-7 7.a) D. L. Comins and A. Dehghani, Tetrahedron Lett., 1992, 33, 6299. b) G. T. Crisp and A. G. Meyer, J. Org. Chem., 1992, 57, 6972. c) J. E. MuMurry and W. J. Scott, Tetrahedron Lett., 1983, 24, 979. 10.1016/S0040-4020(98)00861-8 8. M. Ishikura, Y. Matsuzaki, I. Agata, and N. Katagiri, Tetrahedron, 1998, 54, 13929. 9. The stereochemistry of 5b and 5b’ was determined based on NOE experiments.5 A distinctive enhancement of 6a-H and 9-H upon irradiation of 10a-H in 5b’. 10.1002/0471264180.or047.02 10. R. D. Little, M. R. Masjedizadeh, O. Wallquist, and J. I. McLoughlin, Organic Reactions, 1995, 47, 315. 11. The two directions of the addition can occur on the same (β-addition) and opposite sides (α-addition) of the tert-Bu group. In view of the hindered nature of the tert-Bu group (Fig.), it is conceivable that the spatial repulsion between the indole ring and tert-Bu group renders the β-addition slow relative to the α-addition. 10.1002/0471264180.or045.01 12. K. L. Habermas, S. E. Denmark, and T. K. Jones, Organic Reactions, 1994, 45, 1. 13. Formation of 5b’ via cyclopentadienylcation. 14. G. M. Rubotton, J. M. Gruber, H. D. Juve Jr., and D. A. Charleson, Org. Synth., 1990, Col. Vol. 7, 282. 15. H. J. Reich, J. M. Renga, I. L. Reich, J. Am. Chem. Soc., 1975, 97, 5434.