Synthesis of 3-hydroxyindolin-2-one alkaloids, (±)-donaxaridine and (±)-convolutamydines A and E, through enolization-Claisen rearrangement of 2-allyloxyindolin-3-ones

Tetrahedron

Volumn 60, Issue 15, 2004, Pages 3493-3503

  Kawasaki, Tomomi ^a   Nagaoka, Miyuki ^a   Satoh, Tomoko ^a   Okamoto, Ayako ^a   Ukon, Rie ^a   Ogawa, Atsuyo ^a  

^a MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Allylalcohol; DBU; Molybdenum peroxide; Osmium tetraoxide; Wacker oxidation

Indexed keywords

3 HYDROXYINDOLIN 2 ONE; ALKALOID DERIVATIVE; CONVOLUTAMYDINE A; CONVOLUTAMYDINE E; DONAXARIDINE; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CLAISEN REARRANGEMENT; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; STRUCTURE ANALYSIS;

EID: 1642276051     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.02.031     Document Type: Article

References (69)

1. Isolation: (a) Ubaidullaev, K. A.; Shakirov, R.; Yunosov, S. Y. Khim. Prir. Soedin. 1976, 12, 553 - 554. Synthesis: (b) Rasmussen, H. B.; MacLeod, J. K. J. Nat. Prod. 1997, 60, 1152-1154.
2. Isolation: (a) Ubaidullaev, K. A.; Shakirov, R.; Yunosov, S. Y. Khim. Prir. Soedin. 1976, 12, 553 - 554. Synthesis: (b) Rasmussen, H. B.; MacLeod, J. K. J. Nat. Prod. 1997, 60, 1152-1154.
3. Isolation: (a) Kamano, Y.; Zhang, H.-P.; Ichihara, Y.; Kizu, H.; Komiyama, K.; Pettit, G. R. Tetrahedron Lett. 1995, 36, 2783-2784. (b) Zhang, H.-P.; Kamano, Y.; Ichihara, Y.; Kizu, H.; Komiyama, K.; Itokawa, H.; Pettit, G. R. Tetrahedron 1995, 51, 5523-5528. (c) Kamano, Y.; Kotake, A.; Hashima, H.; Hayakawa, I.; Hiraide, H.; Zhang, H.-P.; Kizu, H.; Komiyama, K.; Hayashi, M.; Pettit, G. R. Collect. Czech. Chem. Commun. 1999, 64, 1147-1153. Synthesis: (d) Garden, S. J.; Torres, J. C.; Ferreira, A. A.; Silva, R. B.; Pinto, A. C. Tetrahedron Lett. 1997, 38, 1501-1504. (e) Miah, S.; Moody, C. J.; Richards, I. C.; Slawin, A. M. Z. J. Chem. Soc., Perkin Trans. 1 1997, 2405-2412. (f) Jnaneshwara, G. K.; Bedekar, A. V.; Deshpande, V. H. Synth. Commun. 1999, 29, 3627-3633. (g) Jnaneshwar, G. K.; Deshpande, V. H. J. Chem. Res. (S) 1999, 632-633.
4. Isolation: (a) Kamano, Y.; Zhang, H.-P.; Ichihara, Y.; Kizu, H.; Komiyama, K.; Pettit, G. R. Tetrahedron Lett. 1995, 36, 2783-2784. (b) Zhang, H.-P.; Kamano, Y.; Ichihara, Y.; Kizu, H.; Komiyama, K.; Itokawa, H.; Pettit, G. R. Tetrahedron 1995, 51, 5523-5528. (c) Kamano, Y.; Kotake, A.; Hashima, H.; Hayakawa, I.; Hiraide, H.; Zhang, H.-P.; Kizu, H.; Komiyama, K.; Hayashi, M.; Pettit, G. R. Collect. Czech. Chem. Commun. 1999, 64, 1147-1153. Synthesis: (d) Garden, S. J.; Torres, J. C.; Ferreira, A. A.; Silva, R. B.; Pinto, A. C. Tetrahedron Lett. 1997, 38, 1501-1504. (e) Miah, S.; Moody, C. J.; Richards, I. C.; Slawin, A. M. Z. J. Chem. Soc., Perkin Trans. 1 1997, 2405-2412. (f) Jnaneshwara, G. K.; Bedekar, A. V.; Deshpande, V. H. Synth. Commun. 1999, 29, 3627-3633. (g) Jnaneshwar, G. K.; Deshpande, V. H. J. Chem. Res. (S) 1999, 632-633.
5. Isolation: (a) Kamano, Y.; Zhang, H.-P.; Ichihara, Y.; Kizu, H.; Komiyama, K.; Pettit, G. R. Tetrahedron Lett. 1995, 36, 2783-2784. (b) Zhang, H.-P.; Kamano, Y.; Ichihara, Y.; Kizu, H.; Komiyama, K.; Itokawa, H.; Pettit, G. R. Tetrahedron 1995, 51, 5523-5528. (c) Kamano, Y.; Kotake, A.; Hashima, H.; Hayakawa, I.; Hiraide, H.; Zhang, H.-P.; Kizu, H.; Komiyama, K.; Hayashi, M.; Pettit, G. R. Collect. Czech. Chem. Commun. 1999, 64, 1147-1153. Synthesis: (d) Garden, S. J.; Torres, J. C.; Ferreira, A. A.; Silva, R. B.; Pinto, A. C. Tetrahedron Lett. 1997, 38, 1501-1504. (e) Miah, S.; Moody, C. J.; Richards, I. C.; Slawin, A. M. Z. J. Chem. Soc., Perkin Trans. 1 1997, 2405-2412. (f) Jnaneshwara, G. K.; Bedekar, A. V.; Deshpande, V. H. Synth. Commun. 1999, 29, 3627-3633. (g) Jnaneshwar, G. K.; Deshpande, V. H. J. Chem. Res. (S) 1999, 632-633.
6. Isolation: (a) Kamano, Y.; Zhang, H.-P.; Ichihara, Y.; Kizu, H.; Komiyama, K.; Pettit, G. R. Tetrahedron Lett. 1995, 36, 2783-2784. (b) Zhang, H.-P.; Kamano, Y.; Ichihara, Y.; Kizu, H.; Komiyama, K.; Itokawa, H.; Pettit, G. R. Tetrahedron 1995, 51, 5523-5528. (c) Kamano, Y.; Kotake, A.; Hashima, H.; Hayakawa, I.; Hiraide, H.; Zhang, H.-P.; Kizu, H.; Komiyama, K.; Hayashi, M.; Pettit, G. R. Collect. Czech. Chem. Commun. 1999, 64, 1147-1153. Synthesis: (d) Garden, S. J.; Torres, J. C.; Ferreira, A. A.; Silva, R. B.; Pinto, A. C. Tetrahedron Lett. 1997, 38, 1501-1504. (e) Miah, S.; Moody, C. J.; Richards, I. C.; Slawin, A. M. Z. J. Chem. Soc., Perkin Trans. 1 1997, 2405-2412. (f) Jnaneshwara, G. K.; Bedekar, A. V.; Deshpande, V. H. Synth. Commun. 1999, 29, 3627-3633. (g) Jnaneshwar, G. K.; Deshpande, V. H. J. Chem. Res. (S) 1999, 632-633.
7. Isolation: (a) Kamano, Y.; Zhang, H.-P.; Ichihara, Y.; Kizu, H.; Komiyama, K.; Pettit, G. R. Tetrahedron Lett. 1995, 36, 2783-2784. (b) Zhang, H.-P.; Kamano, Y.; Ichihara, Y.; Kizu, H.; Komiyama, K.; Itokawa, H.; Pettit, G. R. Tetrahedron 1995, 51, 5523-5528. (c) Kamano, Y.; Kotake, A.; Hashima, H.; Hayakawa, I.; Hiraide, H.; Zhang, H.-P.; Kizu, H.; Komiyama, K.; Hayashi, M.; Pettit, G. R. Collect. Czech. Chem. Commun. 1999, 64, 1147-1153. Synthesis: (d) Garden, S. J.; Torres, J. C.; Ferreira, A. A.; Silva, R. B.; Pinto, A. C. Tetrahedron Lett. 1997, 38, 1501-1504. (e) Miah, S.; Moody, C. J.; Richards, I. C.; Slawin, A. M. Z. J. Chem. Soc., Perkin Trans. 1 1997, 2405-2412. (f) Jnaneshwara, G. K.; Bedekar, A. V.; Deshpande, V. H. Synth. Commun. 1999, 29, 3627-3633. (g) Jnaneshwar, G. K.; Deshpande, V. H. J. Chem. Res. (S) 1999, 632-633.
8. Isolation: (a) Kamano, Y.; Zhang, H.-P.; Ichihara, Y.; Kizu, H.; Komiyama, K.; Pettit, G. R. Tetrahedron Lett. 1995, 36, 2783-2784. (b) Zhang, H.-P.; Kamano, Y.; Ichihara, Y.; Kizu, H.; Komiyama, K.; Itokawa, H.; Pettit, G. R. Tetrahedron 1995, 51, 5523-5528. (c) Kamano, Y.; Kotake, A.; Hashima, H.; Hayakawa, I.; Hiraide, H.; Zhang, H.-P.; Kizu, H.; Komiyama, K.; Hayashi, M.; Pettit, G. R. Collect. Czech. Chem. Commun. 1999, 64, 1147-1153. Synthesis: (d) Garden, S. J.; Torres, J. C.; Ferreira, A. A.; Silva, R. B.; Pinto, A. C. Tetrahedron Lett. 1997, 38, 1501-1504. (e) Miah, S.; Moody, C. J.; Richards, I. C.; Slawin, A. M. Z. J. Chem. Soc., Perkin Trans. 1 1997, 2405-2412. (f) Jnaneshwara, G. K.; Bedekar, A. V.; Deshpande, V. H. Synth. Commun. 1999, 29, 3627-3633. (g) Jnaneshwar, G. K.; Deshpande, V. H. J. Chem. Res. (S) 1999, 632-633.
9. Isolation: (a) Kamano, Y.; Zhang, H.-P.; Ichihara, Y.; Kizu, H.; Komiyama, K.; Pettit, G. R. Tetrahedron Lett. 1995, 36, 2783-2784. (b) Zhang, H.-P.; Kamano, Y.; Ichihara, Y.; Kizu, H.; Komiyama, K.; Itokawa, H.; Pettit, G. R. Tetrahedron 1995, 51, 5523-5528. (c) Kamano, Y.; Kotake, A.; Hashima, H.; Hayakawa, I.; Hiraide, H.; Zhang, H.-P.; Kizu, H.; Komiyama, K.; Hayashi, M.; Pettit, G. R. Collect. Czech. Chem. Commun. 1999, 64, 1147-1153. Synthesis: (d) Garden, S. J.; Torres, J. C.; Ferreira, A. A.; Silva, R. B.; Pinto, A. C. Tetrahedron Lett. 1997, 38, 1501-1504. (e) Miah, S.; Moody, C. J.; Richards, I. C.; Slawin, A. M. Z. J. Chem. Soc., Perkin Trans. 1 1997, 2405-2412. (f) Jnaneshwara, G. K.; Bedekar, A. V.; Deshpande, V. H. Synth. Commun. 1999, 29, 3627-3633. (g) Jnaneshwar, G. K.; Deshpande, V. H. J. Chem. Res. (S) 1999, 632-633.
10. Isolation: (a) Monde, K.; Sasaki, K.; Shirata, A.; Takasugi, M. Phytochemistry 1991, 30, 2915-2917. Synthesis: (b) Suchy, M.; Kutschy, P.; Monde, K.; Goto, H.; Harada, N.; Takasugi, M.; Dzurilla, M.; Balentova, E. J. Org. Chem. 2001, 66, 3940-3947.
11. Isolation: (a) Monde, K.; Sasaki, K.; Shirata, A.; Takasugi, M. Phytochemistry 1991, 30, 2915-2917. Synthesis: (b) Suchy, M.; Kutschy, P.; Monde, K.; Goto, H.; Harada, N.; Takasugi, M.; Dzurilla, M.; Balentova, E. J. Org. Chem. 2001, 66, 3940-3947.
12. Jimenez, J. I.; Huber, U.; Moore, R. E.; Patterson, G. M. L. J. Nat. Prod. 1999, 62, 569-572.
13. Fréchard, A.; Fabre, N.; Péan, C.; Montaut, S.; Fauvel, M.-T.; Rollin, P.; Fourasté, I. Tetrahedron Lett. 2001, 42, 9015-9017.
14. Isolation: (a) Koguchi, Y.; Kohno, J.; Nishio, M.; Takahashi, K.; Okuda, T.; Ohnuki, T.; Komatsubara, S. J. Antibiot. 2000, 53, 105-109. Structure: (b) Khono, J.; Koguchi, Y.; Nishio, M.; Nakao, K.; Juroda, M.; Shimizu, R.; Ohnuki, T.; Komatsubara, S. J. Org. Chem. 2000, 65, 990-995. Synthesis: (c) Lin, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2002, 41, 512-515. (d) Albrecht, B. K.; Williams, R. M. Org. Lett. 2003, 5, 197-200.
15. Isolation: (a) Koguchi, Y.; Kohno, J.; Nishio, M.; Takahashi, K.; Okuda, T.; Ohnuki, T.; Komatsubara, S. J. Antibiot. 2000, 53, 105-109. Structure: (b) Khono, J.; Koguchi, Y.; Nishio, M.; Nakao, K.; Juroda, M.; Shimizu, R.; Ohnuki, T.; Komatsubara, S. J. Org. Chem. 2000, 65, 990-995. Synthesis: (c) Lin, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2002, 41, 512-515. (d) Albrecht, B. K.; Williams, R. M. Org. Lett. 2003, 5, 197-200.
16. Isolation: (a) Koguchi, Y.; Kohno, J.; Nishio, M.; Takahashi, K.; Okuda, T.; Ohnuki, T.; Komatsubara, S. J. Antibiot. 2000, 53, 105-109. Structure: (b) Khono, J.; Koguchi, Y.; Nishio, M.; Nakao, K.; Juroda, M.; Shimizu, R.; Ohnuki, T.; Komatsubara, S. J. Org. Chem. 2000, 65, 990-995. Synthesis: (c) Lin, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2002, 41, 512-515. (d) Albrecht, B. K.; Williams, R. M. Org. Lett. 2003, 5, 197-200.
17. Isolation: (a) Koguchi, Y.; Kohno, J.; Nishio, M.; Takahashi, K.; Okuda, T.; Ohnuki, T.; Komatsubara, S. J. Antibiot. 2000, 53, 105-109. Structure: (b) Khono, J.; Koguchi, Y.; Nishio, M.; Nakao, K.; Juroda, M.; Shimizu, R.; Ohnuki, T.; Komatsubara, S. J. Org. Chem. 2000, 65, 990-995. Synthesis: (c) Lin, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2002, 41, 512-515. (d) Albrecht, B. K.; Williams, R. M. Org. Lett. 2003, 5, 197-200.
18. Others: (a) Pedras, M. S.; Montaut, S.; Xu, Y.; Khan, A. Q.; Loukaci, A. Chem. Commun. 2001, 1572-1573. (b) Hewawasam, P.; Erway, M.; Moon, S. L.; Knipe, J.; Weiner, H.; Boissard, C. G.; Post-Munson, D. J.; Gao, Q.; Huang, S.; Gribkoff, V. K.; Meanwell, N. A. J. Med. Chem. 2002, 45, 1487-1499. (c) Codding, P. W.; Lee, T. A.; Richardson, J. F. J. Med. Chem. 1984, 27, 649-654. (d) Popp, F. D.; Pajouhesh, H. J. Pharm. Sci. 1982, 71, 1052-1054.
19. Others: (a) Pedras, M. S.; Montaut, S.; Xu, Y.; Khan, A. Q.; Loukaci, A. Chem. Commun. 2001, 1572-1573. (b) Hewawasam, P.; Erway, M.; Moon, S. L.; Knipe, J.; Weiner, H.; Boissard, C. G.; Post-Munson, D. J.; Gao, Q.; Huang, S.; Gribkoff, V. K.; Meanwell, N. A. J. Med. Chem. 2002, 45, 1487-1499. (c) Codding, P. W.; Lee, T. A.; Richardson, J. F. J. Med. Chem. 1984, 27, 649-654. (d) Popp, F. D.; Pajouhesh, H. J. Pharm. Sci. 1982, 71, 1052-1054.
20. Others: (a) Pedras, M. S.; Montaut, S.; Xu, Y.; Khan, A. Q.; Loukaci, A. Chem. Commun. 2001, 1572-1573. (b) Hewawasam, P.; Erway, M.; Moon, S. L.; Knipe, J.; Weiner, H.; Boissard, C. G.; Post-Munson, D. J.; Gao, Q.; Huang, S.; Gribkoff, V. K.; Meanwell, N. A. J. Med. Chem. 2002, 45, 1487-1499. (c) Codding, P. W.; Lee, T. A.; Richardson, J. F. J. Med. Chem. 1984, 27, 649-654. (d) Popp, F. D.; Pajouhesh, H. J. Pharm. Sci. 1982, 71, 1052-1054.
21. Others: (a) Pedras, M. S.; Montaut, S.; Xu, Y.; Khan, A. Q.; Loukaci, A. Chem. Commun. 2001, 1572-1573. (b) Hewawasam, P.; Erway, M.; Moon, S. L.; Knipe, J.; Weiner, H.; Boissard, C. G.; Post-Munson, D. J.; Gao, Q.; Huang, S.; Gribkoff, V. K.; Meanwell, N. A. J. Med. Chem. 2002, 45, 1487-1499. (c) Codding, P. W.; Lee, T. A.; Richardson, J. F. J. Med. Chem. 1984, 27, 649-654. (d) Popp, F. D.; Pajouhesh, H. J. Pharm. Sci. 1982, 71, 1052-1054.
22. Sundberg, R. J. The chemistry of indoles; Academic: New York, 1970; pp 341-392.
23. Aldol condensation of isatins with methylketones: (a) Garden, S. J.; da Silva, R. B.; Pinto, A. C. Tetrahedron 2002, 58, 8399-8412. (b) Beccalli, E. M. ; Marchesini, A.; Pilati, T. J. Chem. Soc., Perkin Trans. 1 1994, 579-587. (c) Pajouhesh, H.; Parson, R.; Popp, F. D. J. Pharm. Sci. 1983, 72, 318-321. (d) Popp, F. D. J. Heterocycl. Chem. 1982, 19, 589-592.
24. Aldol condensation of isatins with methylketones: (a) Garden, S. J.; da Silva, R. B.; Pinto, A. C. Tetrahedron 2002, 58, 8399-8412. (b) Beccalli, E. M. ; Marchesini, A.; Pilati, T. J. Chem. Soc., Perkin Trans. 1 1994, 579-587. (c) Pajouhesh, H.; Parson, R.; Popp, F. D. J. Pharm. Sci. 1983, 72, 318-321. (d) Popp, F. D. J. Heterocycl. Chem. 1982, 19, 589-592.
25. Aldol condensation of isatins with methylketones: (a) Garden, S. J.; da Silva, R. B.; Pinto, A. C. Tetrahedron 2002, 58, 8399-8412. (b) Beccalli, E. M. ; Marchesini, A.; Pilati, T. J. Chem. Soc., Perkin Trans. 1 1994, 579-587. (c) Pajouhesh, H.; Parson, R.; Popp, F. D. J. Pharm. Sci. 1983, 72, 318-321. (d) Popp, F. D. J. Heterocycl. Chem. 1982, 19, 589-592.
26. Aldol condensation of isatins with methylketones: (a) Garden, S. J.; da Silva, R. B.; Pinto, A. C. Tetrahedron 2002, 58, 8399-8412. (b) Beccalli, E. M. ; Marchesini, A.; Pilati, T. J. Chem. Soc., Perkin Trans. 1 1994, 579-587. (c) Pajouhesh, H.; Parson, R.; Popp, F. D. J. Pharm. Sci. 1983, 72, 318-321. (d) Popp, F. D. J. Heterocycl. Chem. 1982, 19, 589-592.
27. Addition of Grignard reagent to isatins: (a) Sharma, V. M.; Prasanna, P. ; Seshu, K. V. A.; Renuka, B.; Rao, C. V. L.; Kumar, G. S.; Narasimhulu, C. P.; Babu, P. A.; Puranik, R. C.; Subramanyam, D.; Venkateswarlu, A.; Rajagopal, S.; Kumar, K. B. S.; Rao, C. S.; Mamidi, N. V. S. R.; Deevi, D. S.; Ajaykumar, R.; Rajagopalan, R. Bioorg. Med. Chem. Lett. 2002, 12, 2303-2307. (b) Hewawasam, P. ; Gribkoff, V. K.; Pendri, Y.; Dworetzky, S. I.; Meanwell, N. A.; Martinez, E.; Boissard, C. G.; Post-Munson, D. J.; Trojnacki, J. T.; Yeleswaram, K.; Pajor, L. M.; Knipe, J.; Gao, Q.; Perrone, R.; Starrett, J. E. Bioorg. Med. Chem. Lett. 2002, 12, 1023-1026. (c) Hewawasam, P.; Erway, M. Tetrahedron Lett. 1998, 39, 3981-3984.
28. Addition of Grignard reagent to isatins: (a) Sharma, V. M.; Prasanna, P. ; Seshu, K. V. A.; Renuka, B.; Rao, C. V. L.; Kumar, G. S.; Narasimhulu, C. P.; Babu, P. A.; Puranik, R. C.; Subramanyam, D.; Venkateswarlu, A.; Rajagopal, S.; Kumar, K. B. S.; Rao, C. S.; Mamidi, N. V. S. R.; Deevi, D. S.; Ajaykumar, R.; Rajagopalan, R. Bioorg. Med. Chem. Lett. 2002, 12, 2303-2307. (b) Hewawasam, P. ; Gribkoff, V. K.; Pendri, Y.; Dworetzky, S. I.; Meanwell, N. A.; Martinez, E.; Boissard, C. G.; Post-Munson, D. J.; Trojnacki, J. T.; Yeleswaram, K.; Pajor, L. M.; Knipe, J.; Gao, Q.; Perrone, R.; Starrett, J. E. Bioorg. Med. Chem. Lett. 2002, 12, 1023-1026. (c) Hewawasam, P.; Erway, M. Tetrahedron Lett. 1998, 39, 3981-3984.
29. Addition of Grignard reagent to isatins: (a) Sharma, V. M.; Prasanna, P. ; Seshu, K. V. A.; Renuka, B.; Rao, C. V. L.; Kumar, G. S.; Narasimhulu, C. P.; Babu, P. A.; Puranik, R. C.; Subramanyam, D.; Venkateswarlu, A.; Rajagopal, S.; Kumar, K. B. S.; Rao, C. S.; Mamidi, N. V. S. R.; Deevi, D. S.; Ajaykumar, R.; Rajagopalan, R. Bioorg. Med. Chem. Lett. 2002, 12, 2303-2307. (b) Hewawasam, P. ; Gribkoff, V. K.; Pendri, Y.; Dworetzky, S. I.; Meanwell, N. A.; Martinez, E.; Boissard, C. G.; Post-Munson, D. J.; Trojnacki, J. T.; Yeleswaram, K.; Pajor, L. M.; Knipe, J.; Gao, Q.; Perrone, R.; Starrett, J. E. Bioorg. Med. Chem. Lett. 2002, 12, 1023-1026. (c) Hewawasam, P.; Erway, M. Tetrahedron Lett. 1998, 39, 3981-3984.
30. Baylis-Hilman reaction of isatins with enones: Garden, S. J.; Skakle, J. M. S. Tetrahedron Lett. 2002, 43, 1969-1972.
31. Photoinduced addition of enol ethers to isatin: Zhang, Y.; Xue, J.; Gao, Y.; Fun, H.-K.; Xu, J.-H. J. Chem. Soc., Perkin Trans. 1 2002, 345-353.
32. Oxidation of 3-substituted indoles: (a) Peyrot, F.; Martin, M.-T.; Migault, J.; Ducrocq, C. Eur. J. Org. Chem. 2003, 172-181. (b) Alvarez, R. G.; Hunter, I. S.; Suckling, C. J.; Thomas, M.; Vitinius, U. Tetrahedron 2001, 57, 8581-8587.
33. Oxidation of 3-substituted indoles: (a) Peyrot, F.; Martin, M.-T.; Migault, J.; Ducrocq, C. Eur. J. Org. Chem. 2003, 172-181. (b) Alvarez, R. G.; Hunter, I. S.; Suckling, C. J.; Thomas, M.; Vitinius, U. Tetrahedron 2001, 57, 8581-8587.
34. Oxidation of 3-substituted indolin-2-ones: (a) Takayama, H.; Shimizu, T. ; Sada, H.; Harada, Y.; Kitajima, M.; Aimi, N. Tetrahedron 1999, 55, 6841-6846. (b) Miah, S.; Moody, C. J.; Richards, I. C.; Slawin, A. M. Z. J. Chem. Soc., Perkin Trans. 1 1997, 2405-2412. (c) Hewawasam, P.; Meanwell, N. A.; Gribkoff, V. K.; Dworetzky, S. I.; Boissard, C. G. Bioorg. Med. Chem. Lett. 1997, 7, 1255-1260.
35. Oxidation of 3-substituted indolin-2-ones: (a) Takayama, H.; Shimizu, T. ; Sada, H.; Harada, Y.; Kitajima, M.; Aimi, N. Tetrahedron 1999, 55, 6841-6846. (b) Miah, S.; Moody, C. J.; Richards, I. C.; Slawin, A. M. Z. J. Chem. Soc., Perkin Trans. 1 1997, 2405-2412. (c) Hewawasam, P.; Meanwell, N. A.; Gribkoff, V. K.; Dworetzky, S. I.; Boissard, C. G. Bioorg. Med. Chem. Lett. 1997, 7, 1255-1260.
36. Oxidation of 3-substituted indolin-2-ones: (a) Takayama, H.; Shimizu, T. ; Sada, H.; Harada, Y.; Kitajima, M.; Aimi, N. Tetrahedron 1999, 55, 6841-6846. (b) Miah, S.; Moody, C. J.; Richards, I. C.; Slawin, A. M. Z. J. Chem. Soc., Perkin Trans. 1 1997, 2405-2412. (c) Hewawasam, P.; Meanwell, N. A.; Gribkoff, V. K.; Dworetzky, S. I.; Boissard, C. G. Bioorg. Med. Chem. Lett. 1997, 7, 1255-1260.
37. Oxidation of 3-alkylideneindolin-2-ones: (a) Lin, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2002, 41, 512-515. (b) Lin, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 1967-1970. (c) Albrecht, B. K.; Williams, R. M. Org. Lett. 2003, 5, 197-200. (d) Inoue, M.; Furuyama, H.; Sakazaki, H.; Hirama, M. Org. Lett. 2001, 3, 2863-2865.
38. Oxidation of 3-alkylideneindolin-2-ones: (a) Lin, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2002, 41, 512-515. (b) Lin, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 1967-1970. (c) Albrecht, B. K.; Williams, R. M. Org. Lett. 2003, 5, 197-200. (d) Inoue, M.; Furuyama, H.; Sakazaki, H.; Hirama, M. Org. Lett. 2001, 3, 2863-2865.
39. Oxidation of 3-alkylideneindolin-2-ones: (a) Lin, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2002, 41, 512-515. (b) Lin, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 1967-1970. (c) Albrecht, B. K.; Williams, R. M. Org. Lett. 2003, 5, 197-200. (d) Inoue, M.; Furuyama, H.; Sakazaki, H.; Hirama, M. Org. Lett. 2001, 3, 2863-2865.
40. Oxidation of 3-alkylideneindolin-2-ones: (a) Lin, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2002, 41, 512-515. (b) Lin, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 1967-1970. (c) Albrecht, B. K.; Williams, R. M. Org. Lett. 2003, 5, 197-200. (d) Inoue, M.; Furuyama, H.; Sakazaki, H.; Hirama, M. Org. Lett. 2001, 3, 2863-2865.
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43. Miscellaneous reactions: (a) Nicolaou, K. C.; Rao, P. B.; Hao, J.; Reddy, M. V.; Rassias, G.; Huang, X.; Chen, D. Y.-K.; Snyder, S. A. Angew. Chem., Int. Ed. 2003, 42, 1753-1758. (b) Pushechnikov, A. O.; Volochnyuk, D. M.; Tolmachev, A. A. Synlett 2002, 1140-1142. (c) Kafka, S.; Klásek, A.; Kosmrlj, J. J. Org. Chem. 2001, 66, 6394-6399. (d) Klásek, A.; Koistek, K.; Polis, J.; Kosmrlj, J. Tetrahedron 2000, 56, 1551-1560. (e) Dallacker, F.; Sanders, G. Chemiker-Zeitung 1986, 110, 405-411. (f) Bogavac, M.; Arsenijevic, L.; Pavlov, S.; Arsenijevic, V. Arh. Farm. 1985, 35, 99-103.
44. Miscellaneous reactions: (a) Nicolaou, K. C.; Rao, P. B.; Hao, J.; Reddy, M. V.; Rassias, G.; Huang, X.; Chen, D. Y.-K.; Snyder, S. A. Angew. Chem., Int. Ed. 2003, 42, 1753-1758. (b) Pushechnikov, A. O.; Volochnyuk, D. M.; Tolmachev, A. A. Synlett 2002, 1140-1142. (c) Kafka, S.; Klásek, A.; Kosmrlj, J. J. Org. Chem. 2001, 66, 6394-6399. (d) Klásek, A.; Koistek, K.; Polis, J.; Kosmrlj, J. Tetrahedron 2000, 56, 1551-1560. (e) Dallacker, F.; Sanders, G. Chemiker-Zeitung 1986, 110, 405-411. (f) Bogavac, M.; Arsenijevic, L.; Pavlov, S.; Arsenijevic, V. Arh. Farm. 1985, 35, 99-103.
45. Miscellaneous reactions: (a) Nicolaou, K. C.; Rao, P. B.; Hao, J.; Reddy, M. V.; Rassias, G.; Huang, X.; Chen, D. Y.-K.; Snyder, S. A. Angew. Chem., Int. Ed. 2003, 42, 1753-1758. (b) Pushechnikov, A. O.; Volochnyuk, D. M.; Tolmachev, A. A. Synlett 2002, 1140-1142. (c) Kafka, S.; Klásek, A.; Kosmrlj, J. J. Org. Chem. 2001, 66, 6394-6399. (d) Klásek, A.; Koistek, K.; Polis, J.; Kosmrlj, J. Tetrahedron 2000, 56, 1551-1560. (e) Dallacker, F.; Sanders, G. Chemiker-Zeitung 1986, 110, 405-411. (f) Bogavac, M.; Arsenijevic, L.; Pavlov, S.; Arsenijevic, V. Arh. Farm. 1985, 35, 99-103.
46. Miscellaneous reactions: (a) Nicolaou, K. C.; Rao, P. B.; Hao, J.; Reddy, M. V.; Rassias, G.; Huang, X.; Chen, D. Y.-K.; Snyder, S. A. Angew. Chem., Int. Ed. 2003, 42, 1753-1758. (b) Pushechnikov, A. O.; Volochnyuk, D. M.; Tolmachev, A. A. Synlett 2002, 1140-1142. (c) Kafka, S.; Klásek, A.; Kosmrlj, J. J. Org. Chem. 2001, 66, 6394-6399. (d) Klásek, A.; Koistek, K.; Polis, J.; Kosmrlj, J. Tetrahedron 2000, 56, 1551-1560. (e) Dallacker, F.; Sanders, G. Chemiker-Zeitung 1986, 110, 405-411. (f) Bogavac, M.; Arsenijevic, L.; Pavlov, S.; Arsenijevic, V. Arh. Farm. 1985, 35, 99-103.
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