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Volumn , Issue 8, 1998, Pages 1543-1548

Synthesis of N-fused "lactendiynes"

Author keywords

Anticancer compounds; Cycloaromatization; Enediynes; Lactendiynes; Lactams

Indexed keywords


EID: 0001997760     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199808)1998:8<1543::aid-ejoc1543>3.0.co;2-z     Document Type: Article
Times cited : (37)

References (41)
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    • Recent papers in this area: [2a] M. E. Bunnage, K. C. Nicolaou, Chem. Eur. J. 1997, 2, 187-192. [2b] S. Lee, A. Bain, G. A. Sulikowski, W. Solomon, N. Zein, Biorg. Med. Chem. Lett. 1996, 6, 1261-1264. [2C] F. Bosse, A. R. Tunoori, M. E. Maier, Tetrahedron 1997, 53, 9159-9168. [2d] M. Wakayama, H. Nemoto, M. Shibuya, Tetrahedron Lett. 1996, 37, 5397-5400. [2e] H. Mastalerz, T. W. Doyle, J. F. Kadow, D. M. Vyas, Tetrahedron Lett. 1996, 37, 8683-8686. [2f] H. Tanaka, H. Yamada, A. Matsuda, T. Takahashi, Synlett 1997, 381-383. [2g] T. Takahashi, H. Tanaka, H. Yamada, T. Matsumoto, Y. Sugiura, Angew. Chem., Int. Ed. Engl 1997, 36, 1524-1526. [2h] M. E. Maier, D. Langenbacher, Synlett 1996, 682-684. [2i] R. Unno, H. Michishita, H. Inagaki, Y. Suzuki, Y. Baba, T. Jomori, T. Nishikawa, M. Isobe, Bioorg. & Med. Chem. 1997, 5, 987-999 and refs. therein. [2j] C. Roger, D. S. Grierson, Tetrahedron Lett. 1998, 39, 27-30.
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    • Recent papers in this area: [2a] M. E. Bunnage, K. C. Nicolaou, Chem. Eur. J. 1997, 2, 187-192. [2b] S. Lee, A. Bain, G. A. Sulikowski, W. Solomon, N. Zein, Biorg. Med. Chem. Lett. 1996, 6, 1261-1264. [2C] F. Bosse, A. R. Tunoori, M. E. Maier, Tetrahedron 1997, 53, 9159-9168. [2d] M. Wakayama, H. Nemoto, M. Shibuya, Tetrahedron Lett. 1996, 37, 5397-5400. [2e] H. Mastalerz, T. W. Doyle, J. F. Kadow, D. M. Vyas, Tetrahedron Lett. 1996, 37, 8683-8686. [2f] H. Tanaka, H. Yamada, A. Matsuda, T. Takahashi, Synlett 1997, 381-383. [2g] T. Takahashi, H. Tanaka, H. Yamada, T. Matsumoto, Y. Sugiura, Angew. Chem., Int. Ed. Engl 1997, 36, 1524-1526. [2h] M. E. Maier, D. Langenbacher, Synlett 1996, 682-684. [2i] R. Unno, H. Michishita, H. Inagaki, Y. Suzuki, Y. Baba, T. Jomori, T. Nishikawa, M. Isobe, Bioorg. & Med. Chem. 1997, 5, 987-999 and refs. therein. [2j] C. Roger, D. S. Grierson, Tetrahedron Lett. 1998, 39, 27-30.
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    • 0001364702 scopus 로고    scopus 로고
    • Recent papers in this area: [2a] M. E. Bunnage, K. C. Nicolaou, Chem. Eur. J. 1997, 2, 187-192. [2b] S. Lee, A. Bain, G. A. Sulikowski, W. Solomon, N. Zein, Biorg. Med. Chem. Lett. 1996, 6, 1261-1264. [2C] F. Bosse, A. R. Tunoori, M. E. Maier, Tetrahedron 1997, 53, 9159-9168. [2d] M. Wakayama, H. Nemoto, M. Shibuya, Tetrahedron Lett. 1996, 37, 5397-5400. [2e] H. Mastalerz, T. W. Doyle, J. F. Kadow, D. M. Vyas, Tetrahedron Lett. 1996, 37, 8683-8686. [2f] H. Tanaka, H. Yamada, A. Matsuda, T. Takahashi, Synlett 1997, 381-383. [2g] T. Takahashi, H. Tanaka, H. Yamada, T. Matsumoto, Y. Sugiura, Angew. Chem., Int. Ed. Engl 1997, 36, 1524-1526. [2h] M. E. Maier, D. Langenbacher, Synlett 1996, 682-684. [2i] R. Unno, H. Michishita, H. Inagaki, Y. Suzuki, Y. Baba, T. Jomori, T. Nishikawa, M. Isobe, Bioorg. & Med. Chem. 1997, 5, 987-999 and refs. therein. [2j] C. Roger, D. S. Grierson, Tetrahedron Lett. 1998, 39, 27-30.
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    • 0030598009 scopus 로고    scopus 로고
    • Recent papers in this area: [2a] M. E. Bunnage, K. C. Nicolaou, Chem. Eur. J. 1997, 2, 187-192. [2b] S. Lee, A. Bain, G. A. Sulikowski, W. Solomon, N. Zein, Biorg. Med. Chem. Lett. 1996, 6, 1261-1264. [2C] F. Bosse, A. R. Tunoori, M. E. Maier, Tetrahedron 1997, 53, 9159-9168. [2d] M. Wakayama, H. Nemoto, M. Shibuya, Tetrahedron Lett. 1996, 37, 5397-5400. [2e] H. Mastalerz, T. W. Doyle, J. F. Kadow, D. M. Vyas, Tetrahedron Lett. 1996, 37, 8683-8686. [2f] H. Tanaka, H. Yamada, A. Matsuda, T. Takahashi, Synlett 1997, 381-383. [2g] T. Takahashi, H. Tanaka, H. Yamada, T. Matsumoto, Y. Sugiura, Angew. Chem., Int. Ed. Engl 1997, 36, 1524-1526. [2h] M. E. Maier, D. Langenbacher, Synlett 1996, 682-684. [2i] R. Unno, H. Michishita, H. Inagaki, Y. Suzuki, Y. Baba, T. Jomori, T. Nishikawa, M. Isobe, Bioorg. & Med. Chem. 1997, 5, 987-999 and refs. therein. [2j] C. Roger, D. S. Grierson, Tetrahedron Lett. 1998, 39, 27-30.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 5397-5400
    • Wakayama, M.1    Nemoto, H.2    Shibuya, M.3
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    • 16144364301 scopus 로고    scopus 로고
    • Recent papers in this area: [2a] M. E. Bunnage, K. C. Nicolaou, Chem. Eur. J. 1997, 2, 187-192. [2b] S. Lee, A. Bain, G. A. Sulikowski, W. Solomon, N. Zein, Biorg. Med. Chem. Lett. 1996, 6, 1261-1264. [2C] F. Bosse, A. R. Tunoori, M. E. Maier, Tetrahedron 1997, 53, 9159-9168. [2d] M. Wakayama, H. Nemoto, M. Shibuya, Tetrahedron Lett. 1996, 37, 5397-5400. [2e] H. Mastalerz, T. W. Doyle, J. F. Kadow, D. M. Vyas, Tetrahedron Lett. 1996, 37, 8683-8686. [2f] H. Tanaka, H. Yamada, A. Matsuda, T. Takahashi, Synlett 1997, 381-383. [2g] T. Takahashi, H. Tanaka, H. Yamada, T. Matsumoto, Y. Sugiura, Angew. Chem., Int. Ed. Engl 1997, 36, 1524-1526. [2h] M. E. Maier, D. Langenbacher, Synlett 1996, 682-684. [2i] R. Unno, H. Michishita, H. Inagaki, Y. Suzuki, Y. Baba, T. Jomori, T. Nishikawa, M. Isobe, Bioorg. & Med. Chem. 1997, 5, 987-999 and refs. therein. [2j] C. Roger, D. S. Grierson, Tetrahedron Lett. 1998, 39, 27-30.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 8683-8686
    • Mastalerz, H.1    Doyle, T.W.2    Kadow, J.F.3    Vyas, D.M.4
  • 13
    • 0013552811 scopus 로고    scopus 로고
    • Recent papers in this area: [2a] M. E. Bunnage, K. C. Nicolaou, Chem. Eur. J. 1997, 2, 187-192. [2b] S. Lee, A. Bain, G. A. Sulikowski, W. Solomon, N. Zein, Biorg. Med. Chem. Lett. 1996, 6, 1261-1264. [2C] F. Bosse, A. R. Tunoori, M. E. Maier, Tetrahedron 1997, 53, 9159-9168. [2d] M. Wakayama, H. Nemoto, M. Shibuya, Tetrahedron Lett. 1996, 37, 5397-5400. [2e] H. Mastalerz, T. W. Doyle, J. F. Kadow, D. M. Vyas, Tetrahedron Lett. 1996, 37, 8683-8686. [2f] H. Tanaka, H. Yamada, A. Matsuda, T. Takahashi, Synlett 1997, 381-383. [2g] T. Takahashi, H. Tanaka, H. Yamada, T. Matsumoto, Y. Sugiura, Angew. Chem., Int. Ed. Engl 1997, 36, 1524-1526. [2h] M. E. Maier, D. Langenbacher, Synlett 1996, 682-684. [2i] R. Unno, H. Michishita, H. Inagaki, Y. Suzuki, Y. Baba, T. Jomori, T. Nishikawa, M. Isobe, Bioorg. & Med. Chem. 1997, 5, 987-999 and refs. therein. [2j] C. Roger, D. S. Grierson, Tetrahedron Lett. 1998, 39, 27-30.
    • (1997) Synlett , pp. 381-383
    • Tanaka, H.1    Yamada, H.2    Matsuda, A.3    Takahashi, T.4
  • 14
    • 0030799834 scopus 로고    scopus 로고
    • Recent papers in this area: [2a] M. E. Bunnage, K. C. Nicolaou, Chem. Eur. J. 1997, 2, 187-192. [2b] S. Lee, A. Bain, G. A. Sulikowski, W. Solomon, N. Zein, Biorg. Med. Chem. Lett. 1996, 6, 1261-1264. [2C] F. Bosse, A. R. Tunoori, M. E. Maier, Tetrahedron 1997, 53, 9159-9168. [2d] M. Wakayama, H. Nemoto, M. Shibuya, Tetrahedron Lett. 1996, 37, 5397-5400. [2e] H. Mastalerz, T. W. Doyle, J. F. Kadow, D. M. Vyas, Tetrahedron Lett. 1996, 37, 8683-8686. [2f] H. Tanaka, H. Yamada, A. Matsuda, T. Takahashi, Synlett 1997, 381-383. [2g] T. Takahashi, H. Tanaka, H. Yamada, T. Matsumoto, Y. Sugiura, Angew. Chem., Int. Ed. Engl 1997, 36, 1524-1526. [2h] M. E. Maier, D. Langenbacher, Synlett 1996, 682-684. [2i] R. Unno, H. Michishita, H. Inagaki, Y. Suzuki, Y. Baba, T. Jomori, T. Nishikawa, M. Isobe, Bioorg. & Med. Chem. 1997, 5, 987-999 and refs. therein. [2j] C. Roger, D. S. Grierson, Tetrahedron Lett. 1998, 39, 27-30.
    • (1997) Angew. Chem., Int. Ed. Engl , vol.36 , pp. 1524-1526
    • Takahashi, T.1    Tanaka, H.2    Yamada, H.3    Matsumoto, T.4    Sugiura, Y.5
  • 15
    • 0007570420 scopus 로고    scopus 로고
    • Recent papers in this area: [2a] M. E. Bunnage, K. C. Nicolaou, Chem. Eur. J. 1997, 2, 187-192. [2b] S. Lee, A. Bain, G. A. Sulikowski, W. Solomon, N. Zein, Biorg. Med. Chem. Lett. 1996, 6, 1261-1264. [2C] F. Bosse, A. R. Tunoori, M. E. Maier, Tetrahedron 1997, 53, 9159-9168. [2d] M. Wakayama, H. Nemoto, M. Shibuya, Tetrahedron Lett. 1996, 37, 5397-5400. [2e] H. Mastalerz, T. W. Doyle, J. F. Kadow, D. M. Vyas, Tetrahedron Lett. 1996, 37, 8683-8686. [2f] H. Tanaka, H. Yamada, A. Matsuda, T. Takahashi, Synlett 1997, 381-383. [2g] T. Takahashi, H. Tanaka, H. Yamada, T. Matsumoto, Y. Sugiura, Angew. Chem., Int. Ed. Engl 1997, 36, 1524-1526. [2h] M. E. Maier, D. Langenbacher, Synlett 1996, 682-684. [2i] R. Unno, H. Michishita, H. Inagaki, Y. Suzuki, Y. Baba, T. Jomori, T. Nishikawa, M. Isobe, Bioorg. & Med. Chem. 1997, 5, 987-999 and refs. therein. [2j] C. Roger, D. S. Grierson, Tetrahedron Lett. 1998, 39, 27-30.
    • (1996) Synlett , pp. 682-684
    • Maier, M.E.1    Langenbacher, D.2
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    • and refs. therein
    • Recent papers in this area: [2a] M. E. Bunnage, K. C. Nicolaou, Chem. Eur. J. 1997, 2, 187-192. [2b] S. Lee, A. Bain, G. A. Sulikowski, W. Solomon, N. Zein, Biorg. Med. Chem. Lett. 1996, 6, 1261-1264. [2C] F. Bosse, A. R. Tunoori, M. E. Maier, Tetrahedron 1997, 53, 9159-9168. [2d] M. Wakayama, H. Nemoto, M. Shibuya, Tetrahedron Lett. 1996, 37, 5397-5400. [2e] H. Mastalerz, T. W. Doyle, J. F. Kadow, D. M. Vyas, Tetrahedron Lett. 1996, 37, 8683-8686. [2f] H. Tanaka, H. Yamada, A. Matsuda, T. Takahashi, Synlett 1997, 381-383. [2g] T. Takahashi, H. Tanaka, H. Yamada, T. Matsumoto, Y. Sugiura, Angew. Chem., Int. Ed. Engl 1997, 36, 1524-1526. [2h] M. E. Maier, D. Langenbacher, Synlett 1996, 682-684. [2i] R. Unno, H. Michishita, H. Inagaki, Y. Suzuki, Y. Baba, T. Jomori, T. Nishikawa, M. Isobe, Bioorg. & Med. Chem. 1997, 5, 987-999 and refs. therein. [2j] C. Roger, D. S. Grierson, Tetrahedron Lett. 1998, 39, 27-30.
    • (1997) Bioorg. & Med. Chem. , vol.5 , pp. 987-999
    • Unno, R.1    Michishita, H.2    Inagaki, H.3    Suzuki, Y.4    Baba, Y.5    Jomori, T.6    Nishikawa, T.7    Isobe, M.8
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    • Recent papers in this area: [2a] M. E. Bunnage, K. C. Nicolaou, Chem. Eur. J. 1997, 2, 187-192. [2b] S. Lee, A. Bain, G. A. Sulikowski, W. Solomon, N. Zein, Biorg. Med. Chem. Lett. 1996, 6, 1261-1264. [2C] F. Bosse, A. R. Tunoori, M. E. Maier, Tetrahedron 1997, 53, 9159-9168. [2d] M. Wakayama, H. Nemoto, M. Shibuya, Tetrahedron Lett. 1996, 37, 5397-5400. [2e] H. Mastalerz, T. W. Doyle, J. F. Kadow, D. M. Vyas, Tetrahedron Lett. 1996, 37, 8683-8686. [2f] H. Tanaka, H. Yamada, A. Matsuda, T. Takahashi, Synlett 1997, 381-383. [2g] T. Takahashi, H. Tanaka, H. Yamada, T. Matsumoto, Y. Sugiura, Angew. Chem., Int. Ed. Engl 1997, 36, 1524-1526. [2h] M. E. Maier, D. Langenbacher, Synlett 1996, 682-684. [2i] R. Unno, H. Michishita, H. Inagaki, Y. Suzuki, Y. Baba, T. Jomori, T. Nishikawa, M. Isobe, Bioorg. & Med. Chem. 1997, 5, 987-999 and refs. therein. [2j] C. Roger, D. S. Grierson, Tetrahedron Lett. 1998, 39, 27-30.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 27-30
    • Roger, C.1    Grierson, D.S.2
  • 19
    • 0029949488 scopus 로고    scopus 로고
    • Other examples of ortho-fused enediynes: [3a] K. C. Nicolaou, E. J. Sorensen, R. Discordia, C.-K. Hwang, R. E. Minto, K. N. Bharucha, R. G. Bergman, Angew. Chem. Int. Ed. Engl. 1992, 31, 1044-1046; Angew. Chem. 1992, 104, 1094-1096. [3b] J. Wang, J. De Clercq, Tetrahedron Lett. 1996, 37, 3395-3398. [3c] M. F. Semmelhack, Y. Gu, D. M. Ho, Tetrahedron Lett. 1997, 38, 5583-5586.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 3395-3398
    • Wang, J.1    De Clercq, J.2
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    • Other examples of ortho-fused enediynes: [3a] K. C. Nicolaou, E. J. Sorensen, R. Discordia, C.-K. Hwang, R. E. Minto, K. N. Bharucha, R. G. Bergman, Angew. Chem. Int. Ed. Engl. 1992, 31, 1044-1046; Angew. Chem. 1992, 104, 1094-1096. [3b] J. Wang, J. De Clercq, Tetrahedron Lett. 1996, 37, 3395-3398. [3c] M. F. Semmelhack, Y. Gu, D. M. Ho, Tetrahedron Lett. 1997, 38, 5583-5586.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 5583-5586
    • Semmelhack, M.F.1    Gu, Y.2    Ho, D.M.3
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    • [4a] L. Banfi, G. Guanti, Angew. Chem. Int. Ed. Engl. 1995, 34, 2393-2395; Angew. Chem. 1995, 107, 2613-2615.
    • (1995) Angew. Chem. , vol.107 , pp. 2613-2615
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    • Thiaenediynes
    • Oxaenediynes: [5a] R. Singh, G. Just, Tetrahedron Lett. 1990, 31, 185-188. Thiaenediynes: [5b] K. Toshima, K. Ohishi, M. Tomishima, S. Matsumura, Heterocycles 1997, 45, 851-855.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 185-188
    • Singh, R.1    Just, G.2


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