Solid-phase synthesis of naltrindole derivatives using Fischer indole synthesis based on one-pot release and cyclization methodology

Organic Letters

Volumn 5, Issue 8, 2003, Pages 1159-1162

  Tanaka, Hiroshi ^a   Ohno, Hiroshi ^b   Kawamura, Kuniaki ^b   Ohtake, Atsushi ^b   Nagase, Hiroshi ^b   Takahashi, Takashi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b TORAY INDUSTRIES INC   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HYDRAZONE DERIVATIVE; INDOLE DERIVATIVE; NALTRINDOLE; DRUG DERIVATIVE; NALTREXONE;

ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; SOLID; TECHNIQUE; CHEMISTRY; COMBINATORIAL CHEMISTRY; SYNTHESIS;

COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; NALTREXONE;

EID: 0037925396     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol020230d     Document Type: Article

References (39)

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15. For solid-phase synthesis of indoles, see: (a) Yun, W.; Mohan, R. Tetrahedron Lett. 1996, 37, 7189-7192. (b) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307-2310. (c) Zhang, H. C.; Brumfield, K. K.; Maryanoff, B. Tetrahedron Lett. 1997, 38, 2439-2442. (d) Arumugan, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 38, 6473-6479. (e) Collini, M. D.; Ellingboe, W. Tetrahedron Lett. 1997, 38, 7963-7966. (f) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317-8320. (g) Zhang, H.-C.; Brumfield, K. K.; Jaroskova, L.; Maryaoff, B. E. Tetrahedron Lett. 1998, 39, 4449-4452. (h) Stephensen, H.; Zaragoza, F. Tetrahedron Lett. 1999, 40, 5799-5802. (i) Zhang, H.-C.; Ye, H.; Moretto, A. F. ; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89-92. (j) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751-4754. (k) Wu, T. Y. H.; Ding, S.; Gray, N. S.; Schultz, P. G. Org. Lett. 2001, 3, 3827-3830. (l) Macleod, C.; Hartley, C. R.; Hamprecht, D. W. Org. Lett. 2002, 4, 75-78. (m) Brase, S.; Gil, C.; Knepper, K. Bioorg. Med. Chem. 2002, 10, 2415-2437. (n) Yamazaki, K.; Kondo, Y. J. Comb. Chem. 2002, 4, 191-192. (o) Wacker, D. A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189-5191.
16. For solid-phase synthesis of indoles, see: (a) Yun, W.; Mohan, R. Tetrahedron Lett. 1996, 37, 7189-7192. (b) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307-2310. (c) Zhang, H. C.; Brumfield, K. K.; Maryanoff, B. Tetrahedron Lett. 1997, 38, 2439-2442. (d) Arumugan, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 38, 6473-6479. (e) Collini, M. D.; Ellingboe, W. Tetrahedron Lett. 1997, 38, 7963-7966. (f) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317-8320. (g) Zhang, H.-C.; Brumfield, K. K.; Jaroskova, L.; Maryaoff, B. E. Tetrahedron Lett. 1998, 39, 4449-4452. (h) Stephensen, H.; Zaragoza, F. Tetrahedron Lett. 1999, 40, 5799-5802. (i) Zhang, H.-C.; Ye, H.; Moretto, A. F. ; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89-92. (j) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751-4754. (k) Wu, T. Y. H.; Ding, S.; Gray, N. S.; Schultz, P. G. Org. Lett. 2001, 3, 3827-3830. (l) Macleod, C.; Hartley, C. R.; Hamprecht, D. W. Org. Lett. 2002, 4, 75-78. (m) Brase, S.; Gil, C.; Knepper, K. Bioorg. Med. Chem. 2002, 10, 2415-2437. (n) Yamazaki, K.; Kondo, Y. J. Comb. Chem. 2002, 4, 191-192. (o) Wacker, D. A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189-5191.
17. For solid-phase synthesis of indoles, see: (a) Yun, W.; Mohan, R. Tetrahedron Lett. 1996, 37, 7189-7192. (b) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307-2310. (c) Zhang, H. C.; Brumfield, K. K.; Maryanoff, B. Tetrahedron Lett. 1997, 38, 2439-2442. (d) Arumugan, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 38, 6473-6479. (e) Collini, M. D.; Ellingboe, W. Tetrahedron Lett. 1997, 38, 7963-7966. (f) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317-8320. (g) Zhang, H.-C.; Brumfield, K. K.; Jaroskova, L.; Maryaoff, B. E. Tetrahedron Lett. 1998, 39, 4449-4452. (h) Stephensen, H.; Zaragoza, F. Tetrahedron Lett. 1999, 40, 5799-5802. (i) Zhang, H.-C.; Ye, H.; Moretto, A. F. ; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89-92. (j) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751-4754. (k) Wu, T. Y. H.; Ding, S.; Gray, N. S.; Schultz, P. G. Org. Lett. 2001, 3, 3827-3830. (l) Macleod, C.; Hartley, C. R.; Hamprecht, D. W. Org. Lett. 2002, 4, 75-78. (m) Brase, S.; Gil, C.; Knepper, K. Bioorg. Med. Chem. 2002, 10, 2415-2437. (n) Yamazaki, K.; Kondo, Y. J. Comb. Chem. 2002, 4, 191-192. (o) Wacker, D. A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189-5191.
18. For solid-phase synthesis of indoles, see: (a) Yun, W.; Mohan, R. Tetrahedron Lett. 1996, 37, 7189-7192. (b) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307-2310. (c) Zhang, H. C.; Brumfield, K. K.; Maryanoff, B. Tetrahedron Lett. 1997, 38, 2439-2442. (d) Arumugan, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 38, 6473-6479. (e) Collini, M. D.; Ellingboe, W. Tetrahedron Lett. 1997, 38, 7963-7966. (f) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317-8320. (g) Zhang, H.-C.; Brumfield, K. K.; Jaroskova, L.; Maryaoff, B. E. Tetrahedron Lett. 1998, 39, 4449-4452. (h) Stephensen, H.; Zaragoza, F. Tetrahedron Lett. 1999, 40, 5799-5802. (i) Zhang, H.-C.; Ye, H.; Moretto, A. F. ; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89-92. (j) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751-4754. (k) Wu, T. Y. H.; Ding, S.; Gray, N. S.; Schultz, P. G. Org. Lett. 2001, 3, 3827-3830. (l) Macleod, C.; Hartley, C. R.; Hamprecht, D. W. Org. Lett. 2002, 4, 75-78. (m) Brase, S.; Gil, C.; Knepper, K. Bioorg. Med. Chem. 2002, 10, 2415-2437. (n) Yamazaki, K.; Kondo, Y. J. Comb. Chem. 2002, 4, 191-192. (o) Wacker, D. A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189-5191.
19. For solid-phase synthesis of indoles, see: (a) Yun, W.; Mohan, R. Tetrahedron Lett. 1996, 37, 7189-7192. (b) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307-2310. (c) Zhang, H. C.; Brumfield, K. K.; Maryanoff, B. Tetrahedron Lett. 1997, 38, 2439-2442. (d) Arumugan, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 38, 6473-6479. (e) Collini, M. D.; Ellingboe, W. Tetrahedron Lett. 1997, 38, 7963-7966. (f) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317-8320. (g) Zhang, H.-C.; Brumfield, K. K.; Jaroskova, L.; Maryaoff, B. E. Tetrahedron Lett. 1998, 39, 4449-4452. (h) Stephensen, H.; Zaragoza, F. Tetrahedron Lett. 1999, 40, 5799-5802. (i) Zhang, H.-C.; Ye, H.; Moretto, A. F. ; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89-92. (j) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751-4754. (k) Wu, T. Y. H.; Ding, S.; Gray, N. S.; Schultz, P. G. Org. Lett. 2001, 3, 3827-3830. (l) Macleod, C.; Hartley, C. R.; Hamprecht, D. W. Org. Lett. 2002, 4, 75-78. (m) Brase, S.; Gil, C.; Knepper, K. Bioorg. Med. Chem. 2002, 10, 2415-2437. (n) Yamazaki, K.; Kondo, Y. J. Comb. Chem. 2002, 4, 191-192. (o) Wacker, D. A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189-5191.
20. For solid-phase synthesis of indoles, see: (a) Yun, W.; Mohan, R. Tetrahedron Lett. 1996, 37, 7189-7192. (b) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307-2310. (c) Zhang, H. C.; Brumfield, K. K.; Maryanoff, B. Tetrahedron Lett. 1997, 38, 2439-2442. (d) Arumugan, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 38, 6473-6479. (e) Collini, M. D.; Ellingboe, W. Tetrahedron Lett. 1997, 38, 7963-7966. (f) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317-8320. (g) Zhang, H.-C.; Brumfield, K. K.; Jaroskova, L.; Maryaoff, B. E. Tetrahedron Lett. 1998, 39, 4449-4452. (h) Stephensen, H.; Zaragoza, F. Tetrahedron Lett. 1999, 40, 5799-5802. (i) Zhang, H.-C.; Ye, H.; Moretto, A. F. ; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89-92. (j) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751-4754. (k) Wu, T. Y. H.; Ding, S.; Gray, N. S.; Schultz, P. G. Org. Lett. 2001, 3, 3827-3830. (l) Macleod, C.; Hartley, C. R.; Hamprecht, D. W. Org. Lett. 2002, 4, 75-78. (m) Brase, S.; Gil, C.; Knepper, K. Bioorg. Med. Chem. 2002, 10, 2415-2437. (n) Yamazaki, K.; Kondo, Y. J. Comb. Chem. 2002, 4, 191-192. (o) Wacker, D. A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189-5191.
21. For solid-phase synthesis of indoles, see: (a) Yun, W.; Mohan, R. Tetrahedron Lett. 1996, 37, 7189-7192. (b) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307-2310. (c) Zhang, H. C.; Brumfield, K. K.; Maryanoff, B. Tetrahedron Lett. 1997, 38, 2439-2442. (d) Arumugan, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 38, 6473-6479. (e) Collini, M. D.; Ellingboe, W. Tetrahedron Lett. 1997, 38, 7963-7966. (f) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317-8320. (g) Zhang, H.-C.; Brumfield, K. K.; Jaroskova, L.; Maryaoff, B. E. Tetrahedron Lett. 1998, 39, 4449-4452. (h) Stephensen, H.; Zaragoza, F. Tetrahedron Lett. 1999, 40, 5799-5802. (i) Zhang, H.-C.; Ye, H.; Moretto, A. F. ; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89-92. (j) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751-4754. (k) Wu, T. Y. H.; Ding, S.; Gray, N. S.; Schultz, P. G. Org. Lett. 2001, 3, 3827-3830. (l) Macleod, C.; Hartley, C. R.; Hamprecht, D. W. Org. Lett. 2002, 4, 75-78. (m) Brase, S.; Gil, C.; Knepper, K. Bioorg. Med. Chem. 2002, 10, 2415-2437. (n) Yamazaki, K.; Kondo, Y. J. Comb. Chem. 2002, 4, 191-192. (o) Wacker, D. A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189-5191.
22. For solid-phase synthesis of indoles, see: (a) Yun, W.; Mohan, R. Tetrahedron Lett. 1996, 37, 7189-7192. (b) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307-2310. (c) Zhang, H. C.; Brumfield, K. K.; Maryanoff, B. Tetrahedron Lett. 1997, 38, 2439-2442. (d) Arumugan, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 38, 6473-6479. (e) Collini, M. D.; Ellingboe, W. Tetrahedron Lett. 1997, 38, 7963-7966. (f) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317-8320. (g) Zhang, H.-C.; Brumfield, K. K.; Jaroskova, L.; Maryaoff, B. E. Tetrahedron Lett. 1998, 39, 4449-4452. (h) Stephensen, H.; Zaragoza, F. Tetrahedron Lett. 1999, 40, 5799-5802. (i) Zhang, H.-C.; Ye, H.; Moretto, A. F. ; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89-92. (j) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751-4754. (k) Wu, T. Y. H.; Ding, S.; Gray, N. S.; Schultz, P. G. Org. Lett. 2001, 3, 3827-3830. (l) Macleod, C.; Hartley, C. R.; Hamprecht, D. W. Org. Lett. 2002, 4, 75-78. (m) Brase, S.; Gil, C.; Knepper, K. Bioorg. Med. Chem. 2002, 10, 2415-2437. (n) Yamazaki, K.; Kondo, Y. J. Comb. Chem. 2002, 4, 191-192. (o) Wacker, D. A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189-5191.
23. For solid-phase synthesis of indoles, see: (a) Yun, W.; Mohan, R. Tetrahedron Lett. 1996, 37, 7189-7192. (b) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307-2310. (c) Zhang, H. C.; Brumfield, K. K.; Maryanoff, B. Tetrahedron Lett. 1997, 38, 2439-2442. (d) Arumugan, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 38, 6473-6479. (e) Collini, M. D.; Ellingboe, W. Tetrahedron Lett. 1997, 38, 7963-7966. (f) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317-8320. (g) Zhang, H.-C.; Brumfield, K. K.; Jaroskova, L.; Maryaoff, B. E. Tetrahedron Lett. 1998, 39, 4449-4452. (h) Stephensen, H.; Zaragoza, F. Tetrahedron Lett. 1999, 40, 5799-5802. (i) Zhang, H.-C.; Ye, H.; Moretto, A. F. ; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89-92. (j) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751-4754. (k) Wu, T. Y. H.; Ding, S.; Gray, N. S.; Schultz, P. G. Org. Lett. 2001, 3, 3827-3830. (l) Macleod, C.; Hartley, C. R.; Hamprecht, D. W. Org. Lett. 2002, 4, 75-78. (m) Brase, S.; Gil, C.; Knepper, K. Bioorg. Med. Chem. 2002, 10, 2415-2437. (n) Yamazaki, K.; Kondo, Y. J. Comb. Chem. 2002, 4, 191-192. (o) Wacker, D. A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189-5191.
24. For solid-phase synthesis of indoles, see: (a) Yun, W.; Mohan, R. Tetrahedron Lett. 1996, 37, 7189-7192. (b) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307-2310. (c) Zhang, H. C.; Brumfield, K. K.; Maryanoff, B. Tetrahedron Lett. 1997, 38, 2439-2442. (d) Arumugan, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 38, 6473-6479. (e) Collini, M. D.; Ellingboe, W. Tetrahedron Lett. 1997, 38, 7963-7966. (f) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317-8320. (g) Zhang, H.-C.; Brumfield, K. K.; Jaroskova, L.; Maryaoff, B. E. Tetrahedron Lett. 1998, 39, 4449-4452. (h) Stephensen, H.; Zaragoza, F. Tetrahedron Lett. 1999, 40, 5799-5802. (i) Zhang, H.-C.; Ye, H.; Moretto, A. F. ; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89-92. (j) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751-4754. (k) Wu, T. Y. H.; Ding, S.; Gray, N. S.; Schultz, P. G. Org. Lett. 2001, 3, 3827-3830. (l) Macleod, C.; Hartley, C. R.; Hamprecht, D. W. Org. Lett. 2002, 4, 75-78. (m) Brase, S.; Gil, C.; Knepper, K. Bioorg. Med. Chem. 2002, 10, 2415-2437. (n) Yamazaki, K.; Kondo, Y. J. Comb. Chem. 2002, 4, 191-192. (o) Wacker, D. A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189-5191.
25. For solid-phase synthesis of indoles, see: (a) Yun, W.; Mohan, R. Tetrahedron Lett. 1996, 37, 7189-7192. (b) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307-2310. (c) Zhang, H. C.; Brumfield, K. K.; Maryanoff, B. Tetrahedron Lett. 1997, 38, 2439-2442. (d) Arumugan, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 38, 6473-6479. (e) Collini, M. D.; Ellingboe, W. Tetrahedron Lett. 1997, 38, 7963-7966. (f) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317-8320. (g) Zhang, H.-C.; Brumfield, K. K.; Jaroskova, L.; Maryaoff, B. E. Tetrahedron Lett. 1998, 39, 4449-4452. (h) Stephensen, H.; Zaragoza, F. Tetrahedron Lett. 1999, 40, 5799-5802. (i) Zhang, H.-C.; Ye, H.; Moretto, A. F. ; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89-92. (j) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751-4754. (k) Wu, T. Y. H.; Ding, S.; Gray, N. S.; Schultz, P. G. Org. Lett. 2001, 3, 3827-3830. (l) Macleod, C.; Hartley, C. R.; Hamprecht, D. W. Org. Lett. 2002, 4, 75-78. (m) Brase, S.; Gil, C.; Knepper, K. Bioorg. Med. Chem. 2002, 10, 2415-2437. (n) Yamazaki, K.; Kondo, Y. J. Comb. Chem. 2002, 4, 191-192. (o) Wacker, D. A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189-5191.
26. For solid-phase synthesis of indoles, see: (a) Yun, W.; Mohan, R. Tetrahedron Lett. 1996, 37, 7189-7192. (b) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307-2310. (c) Zhang, H. C.; Brumfield, K. K.; Maryanoff, B. Tetrahedron Lett. 1997, 38, 2439-2442. (d) Arumugan, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 38, 6473-6479. (e) Collini, M. D.; Ellingboe, W. Tetrahedron Lett. 1997, 38, 7963-7966. (f) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317-8320. (g) Zhang, H.-C.; Brumfield, K. K.; Jaroskova, L.; Maryaoff, B. E. Tetrahedron Lett. 1998, 39, 4449-4452. (h) Stephensen, H.; Zaragoza, F. Tetrahedron Lett. 1999, 40, 5799-5802. (i) Zhang, H.-C.; Ye, H.; Moretto, A. F. ; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89-92. (j) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751-4754. (k) Wu, T. Y. H.; Ding, S.; Gray, N. S.; Schultz, P. G. Org. Lett. 2001, 3, 3827-3830. (l) Macleod, C.; Hartley, C. R.; Hamprecht, D. W. Org. Lett. 2002, 4, 75-78. (m) Brase, S.; Gil, C.; Knepper, K. Bioorg. Med. Chem. 2002, 10, 2415-2437. (n) Yamazaki, K.; Kondo, Y. J. Comb. Chem. 2002, 4, 191-192. (o) Wacker, D. A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189-5191.
27. For solid-phase synthesis of indoles, see: (a) Yun, W.; Mohan, R. Tetrahedron Lett. 1996, 37, 7189-7192. (b) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307-2310. (c) Zhang, H. C.; Brumfield, K. K.; Maryanoff, B. Tetrahedron Lett. 1997, 38, 2439-2442. (d) Arumugan, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 38, 6473-6479. (e) Collini, M. D.; Ellingboe, W. Tetrahedron Lett. 1997, 38, 7963-7966. (f) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317-8320. (g) Zhang, H.-C.; Brumfield, K. K.; Jaroskova, L.; Maryaoff, B. E. Tetrahedron Lett. 1998, 39, 4449-4452. (h) Stephensen, H.; Zaragoza, F. Tetrahedron Lett. 1999, 40, 5799-5802. (i) Zhang, H.-C.; Ye, H.; Moretto, A. F. ; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89-92. (j) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751-4754. (k) Wu, T. Y. H.; Ding, S.; Gray, N. S.; Schultz, P. G. Org. Lett. 2001, 3, 3827-3830. (l) Macleod, C.; Hartley, C. R.; Hamprecht, D. W. Org. Lett. 2002, 4, 75-78. (m) Brase, S.; Gil, C.; Knepper, K. Bioorg. Med. Chem. 2002, 10, 2415-2437. (n) Yamazaki, K.; Kondo, Y. J. Comb. Chem. 2002, 4, 191-192. (o) Wacker, D. A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189-5191.
28. For solid-phase synthesis of indoles, see: (a) Yun, W.; Mohan, R. Tetrahedron Lett. 1996, 37, 7189-7192. (b) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307-2310. (c) Zhang, H. C.; Brumfield, K. K.; Maryanoff, B. Tetrahedron Lett. 1997, 38, 2439-2442. (d) Arumugan, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 38, 6473-6479. (e) Collini, M. D.; Ellingboe, W. Tetrahedron Lett. 1997, 38, 7963-7966. (f) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317-8320. (g) Zhang, H.-C.; Brumfield, K. K.; Jaroskova, L.; Maryaoff, B. E. Tetrahedron Lett. 1998, 39, 4449-4452. (h) Stephensen, H.; Zaragoza, F. Tetrahedron Lett. 1999, 40, 5799-5802. (i) Zhang, H.-C.; Ye, H.; Moretto, A. F. ; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89-92. (j) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751-4754. (k) Wu, T. Y. H.; Ding, S.; Gray, N. S.; Schultz, P. G. Org. Lett. 2001, 3, 3827-3830. (l) Macleod, C.; Hartley, C. R.; Hamprecht, D. W. Org. Lett. 2002, 4, 75-78. (m) Brase, S.; Gil, C.; Knepper, K. Bioorg. Med. Chem. 2002, 10, 2415-2437. (n) Yamazaki, K.; Kondo, Y. J. Comb. Chem. 2002, 4, 191-192. (o) Wacker, D. A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189-5191.
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36. 2. The combined filtrates were evaporated and dried in vacuo to give 10.4 mg of morphinan compound 1aA TFA salt with 93% purity determined by reversed-phase HPLC.
37. Hydroxymethylphenoxyethyl resin was supplied by Watanabe Chemical.
38. Reaction of solid-linked ketone on Wang resin instead of the hydroxymethylphenoxyethyl resin resulted in the reduced purity (79% purity) of 5aA. HPLC-MS analysis of the mixture showed that it contained NTI derivatives beating the 4-hydroxylbenzyl moiety. These results indicate that the acid-stable base polymer is essential for the solid-phase indole formation.
39. 2O:0.1% HCOOH in MeCN 95:5 (0 min) and then 0:100 (8 min). UV: 254 nm.