Synthesis and DNA cleavage study of a 10-membered ring enediyne formed via allylic rearrangement

Journal of Organic Chemistry

Volumn 64, Issue 3, 1999, Pages 682-683

  Dai, Wei Min ^a   Fong, Kin Chiu ^a   Lau, Chi Wai ^a   Zhou, Ling ^b   Hamaguchi, Wataru ^b   Nishimoto, Sei Ichi ^b  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYLDIALKYNE DERIVATIVE; ALLYL COMPOUND; ANTINEOPLASTIC AGENT; DNA; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; DNA CLEAVAGE; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0344334037     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9820263     Document Type: Article

References (44)

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20. Formation of enediynes from stable precursors by reductive elimination: Myers, A. G.; Dragovich, P. S. J. Am. Chem. Soc. 1992, 114, 5859. By acid- or base-induced elimination of alcohols: Petasis, N. A.; Teets, K. A. Tetrahedron Lett. 1993, 34, 805. Yoshimatsu, M.; Yamada, H.; Shimizu, H.; Kataoka, T. J. Chem. Soc., Chem. Commun. 1994, 2107. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Grierson, D. S. Synlett 1993, 20. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Riche, C.; Chiaroni, A.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Shibuya, M.; Sakai, Y.; Naoe, Y. Tetrahedron Lett. 1995, 36, 897. Iida, K.; Hirama, M. J. Am. Chem. Soc. 1995, 117, 8875. Kawata, S.; Yoshimura, F.; Irie, J.; Ehara, H.; Hirama, M. Synlett 1997, 250. Wang, J.; De Clercq, P. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1749. Takahashi, T.; Tanaka, H.; Matsuda, A.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Tetrahedron Lett. 1996, 37, 2433. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1996, 35, 1835. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 1524. By the Corey-Winter reagent: Semmelhack, M. F.; Gallagher, J.; Tetrahedron Lett. 1993, 34, 4121. Semmelhack, M. F.; Gallagher, J. J.; Ding, W.-D.; Krishnamurthy, G.; Babine, R.; Ellestad, G. A. J. Org. Chem. 1994, 59, 4357. By benzylic oxidation: Huber, R. S.; Jones, G. B. Tetrahedron Lett. 1994, 35, 2655. Maier, M. E.; Greiner, B. Liebigs Ann. Chem. 1992, 855. By the Norrish type-II reaction: Nuss, J. M.; Murphy, M. M. Tetrahedron Lett. 1994, 35, 37. By the Diels-Alder or retro-Diels-Alder reaction: Hopf, H.; Theurig, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1099. Hopf, H.; Theurig, M.; Jones, P. G.; Bubenitschek, P. Liebigs Ann. 1996, 1301. Bunnage, M. E.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1110. Bunnage, M. E.; Nicolaou, K. C. Chem. Eur. J. 1997, 3, 187. Review: Maier, M. E. Synlett 1995, 13.
21. Formation of enediynes from stable precursors by reductive elimination: Myers, A. G.; Dragovich, P. S. J. Am. Chem. Soc. 1992, 114, 5859. By acid- or base-induced elimination of alcohols: Petasis, N. A.; Teets, K. A. Tetrahedron Lett. 1993, 34, 805. Yoshimatsu, M.; Yamada, H.; Shimizu, H.; Kataoka, T. J. Chem. Soc., Chem. Commun. 1994, 2107. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Grierson, D. S. Synlett 1993, 20. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Riche, C.; Chiaroni, A.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Shibuya, M.; Sakai, Y.; Naoe, Y. Tetrahedron Lett. 1995, 36, 897. Iida, K.; Hirama, M. J. Am. Chem. Soc. 1995, 117, 8875. Kawata, S.; Yoshimura, F.; Irie, J.; Ehara, H.; Hirama, M. Synlett 1997, 250. Wang, J.; De Clercq, P. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1749. Takahashi, T.; Tanaka, H.; Matsuda, A.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Tetrahedron Lett. 1996, 37, 2433. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1996, 35, 1835. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 1524. By the Corey-Winter reagent: Semmelhack, M. F.; Gallagher, J.; Tetrahedron Lett. 1993, 34, 4121. Semmelhack, M. F.; Gallagher, J. J.; Ding, W.-D.; Krishnamurthy, G.; Babine, R.; Ellestad, G. A. J. Org. Chem. 1994, 59, 4357. By benzylic oxidation: Huber, R. S.; Jones, G. B. Tetrahedron Lett. 1994, 35, 2655. Maier, M. E.; Greiner, B. Liebigs Ann. Chem. 1992, 855. By the Norrish type-II reaction: Nuss, J. M.; Murphy, M. M. Tetrahedron Lett. 1994, 35, 37. By the Diels-Alder or retro-Diels-Alder reaction: Hopf, H.; Theurig, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1099. Hopf, H.; Theurig, M.; Jones, P. G.; Bubenitschek, P. Liebigs Ann. 1996, 1301. Bunnage, M. E.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1110. Bunnage, M. E.; Nicolaou, K. C. Chem. Eur. J. 1997, 3, 187. Review: Maier, M. E. Synlett 1995, 13.
22. Formation of enediynes from stable precursors by reductive elimination: Myers, A. G.; Dragovich, P. S. J. Am. Chem. Soc. 1992, 114, 5859. By acid- or base-induced elimination of alcohols: Petasis, N. A.; Teets, K. A. Tetrahedron Lett. 1993, 34, 805. Yoshimatsu, M.; Yamada, H.; Shimizu, H.; Kataoka, T. J. Chem. Soc., Chem. Commun. 1994, 2107. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Grierson, D. S. Synlett 1993, 20. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Riche, C.; Chiaroni, A.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Shibuya, M.; Sakai, Y.; Naoe, Y. Tetrahedron Lett. 1995, 36, 897. Iida, K.; Hirama, M. J. Am. Chem. Soc. 1995, 117, 8875. Kawata, S.; Yoshimura, F.; Irie, J.; Ehara, H.; Hirama, M. Synlett 1997, 250. Wang, J.; De Clercq, P. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1749. Takahashi, T.; Tanaka, H.; Matsuda, A.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Tetrahedron Lett. 1996, 37, 2433. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1996, 35, 1835. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 1524. By the Corey-Winter reagent: Semmelhack, M. F.; Gallagher, J.; Tetrahedron Lett. 1993, 34, 4121. Semmelhack, M. F.; Gallagher, J. J.; Ding, W.-D.; Krishnamurthy, G.; Babine, R.; Ellestad, G. A. J. Org. Chem. 1994, 59, 4357. By benzylic oxidation: Huber, R. S.; Jones, G. B. Tetrahedron Lett. 1994, 35, 2655. Maier, M. E.; Greiner, B. Liebigs Ann. Chem. 1992, 855. By the Norrish type-II reaction: Nuss, J. M.; Murphy, M. M. Tetrahedron Lett. 1994, 35, 37. By the Diels-Alder or retro-Diels-Alder reaction: Hopf, H.; Theurig, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1099. Hopf, H.; Theurig, M.; Jones, P. G.; Bubenitschek, P. Liebigs Ann. 1996, 1301. Bunnage, M. E.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1110. Bunnage, M. E.; Nicolaou, K. C. Chem. Eur. J. 1997, 3, 187. Review: Maier, M. E. Synlett 1995, 13.
23. Formation of enediynes from stable precursors by reductive elimination: Myers, A. G.; Dragovich, P. S. J. Am. Chem. Soc. 1992, 114, 5859. By acid- or base-induced elimination of alcohols: Petasis, N. A.; Teets, K. A. Tetrahedron Lett. 1993, 34, 805. Yoshimatsu, M.; Yamada, H.; Shimizu, H.; Kataoka, T. J. Chem. Soc., Chem. Commun. 1994, 2107. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Grierson, D. S. Synlett 1993, 20. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Riche, C.; Chiaroni, A.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Shibuya, M.; Sakai, Y.; Naoe, Y. Tetrahedron Lett. 1995, 36, 897. Iida, K.; Hirama, M. J. Am. Chem. Soc. 1995, 117, 8875. Kawata, S.; Yoshimura, F.; Irie, J.; Ehara, H.; Hirama, M. Synlett 1997, 250. Wang, J.; De Clercq, P. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1749. Takahashi, T.; Tanaka, H.; Matsuda, A.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Tetrahedron Lett. 1996, 37, 2433. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1996, 35, 1835. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 1524. By the Corey-Winter reagent: Semmelhack, M. F.; Gallagher, J.; Tetrahedron Lett. 1993, 34, 4121. Semmelhack, M. F.; Gallagher, J. J.; Ding, W.-D.; Krishnamurthy, G.; Babine, R.; Ellestad, G. A. J. Org. Chem. 1994, 59, 4357. By benzylic oxidation: Huber, R. S.; Jones, G. B. Tetrahedron Lett. 1994, 35, 2655. Maier, M. E.; Greiner, B. Liebigs Ann. Chem. 1992, 855. By the Norrish type-II reaction: Nuss, J. M.; Murphy, M. M. Tetrahedron Lett. 1994, 35, 37. By the Diels-Alder or retro-Diels-Alder reaction: Hopf, H.; Theurig, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1099. Hopf, H.; Theurig, M.; Jones, P. G.; Bubenitschek, P. Liebigs Ann. 1996, 1301. Bunnage, M. E.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1110. Bunnage, M. E.; Nicolaou, K. C. Chem. Eur. J. 1997, 3, 187. Review: Maier, M. E. Synlett 1995, 13.
24. Formation of enediynes from stable precursors by reductive elimination: Myers, A. G.; Dragovich, P. S. J. Am. Chem. Soc. 1992, 114, 5859. By acid- or base-induced elimination of alcohols: Petasis, N. A.; Teets, K. A. Tetrahedron Lett. 1993, 34, 805. Yoshimatsu, M.; Yamada, H.; Shimizu, H.; Kataoka, T. J. Chem. Soc., Chem. Commun. 1994, 2107. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Grierson, D. S. Synlett 1993, 20. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Riche, C.; Chiaroni, A.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Shibuya, M.; Sakai, Y.; Naoe, Y. Tetrahedron Lett. 1995, 36, 897. Iida, K.; Hirama, M. J. Am. Chem. Soc. 1995, 117, 8875. Kawata, S.; Yoshimura, F.; Irie, J.; Ehara, H.; Hirama, M. Synlett 1997, 250. Wang, J.; De Clercq, P. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1749. Takahashi, T.; Tanaka, H.; Matsuda, A.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Tetrahedron Lett. 1996, 37, 2433. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1996, 35, 1835. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 1524. By the Corey-Winter reagent: Semmelhack, M. F.; Gallagher, J.; Tetrahedron Lett. 1993, 34, 4121. Semmelhack, M. F.; Gallagher, J. J.; Ding, W.-D.; Krishnamurthy, G.; Babine, R.; Ellestad, G. A. J. Org. Chem. 1994, 59, 4357. By benzylic oxidation: Huber, R. S.; Jones, G. B. Tetrahedron Lett. 1994, 35, 2655. Maier, M. E.; Greiner, B. Liebigs Ann. Chem. 1992, 855. By the Norrish type-II reaction: Nuss, J. M.; Murphy, M. M. Tetrahedron Lett. 1994, 35, 37. By the Diels-Alder or retro-Diels-Alder reaction: Hopf, H.; Theurig, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1099. Hopf, H.; Theurig, M.; Jones, P. G.; Bubenitschek, P. Liebigs Ann. 1996, 1301. Bunnage, M. E.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1110. Bunnage, M. E.; Nicolaou, K. C. Chem. Eur. J. 1997, 3, 187. Review: Maier, M. E. Synlett 1995, 13.
25. Formation of enediynes from stable precursors by reductive elimination: Myers, A. G.; Dragovich, P. S. J. Am. Chem. Soc. 1992, 114, 5859. By acid- or base-induced elimination of alcohols: Petasis, N. A.; Teets, K. A. Tetrahedron Lett. 1993, 34, 805. Yoshimatsu, M.; Yamada, H.; Shimizu, H.; Kataoka, T. J. Chem. Soc., Chem. Commun. 1994, 2107. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Grierson, D. S. Synlett 1993, 20. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Riche, C.; Chiaroni, A.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Shibuya, M.; Sakai, Y.; Naoe, Y. Tetrahedron Lett. 1995, 36, 897. Iida, K.; Hirama, M. J. Am. Chem. Soc. 1995, 117, 8875. Kawata, S.; Yoshimura, F.; Irie, J.; Ehara, H.; Hirama, M. Synlett 1997, 250. Wang, J.; De Clercq, P. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1749. Takahashi, T.; Tanaka, H.; Matsuda, A.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Tetrahedron Lett. 1996, 37, 2433. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1996, 35, 1835. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 1524. By the Corey-Winter reagent: Semmelhack, M. F.; Gallagher, J.; Tetrahedron Lett. 1993, 34, 4121. Semmelhack, M. F.; Gallagher, J. J.; Ding, W.-D.; Krishnamurthy, G.; Babine, R.; Ellestad, G. A. J. Org. Chem. 1994, 59, 4357. By benzylic oxidation: Huber, R. S.; Jones, G. B. Tetrahedron Lett. 1994, 35, 2655. Maier, M. E.; Greiner, B. Liebigs Ann. Chem. 1992, 855. By the Norrish type-II reaction: Nuss, J. M.; Murphy, M. M. Tetrahedron Lett. 1994, 35, 37. By the Diels-Alder or retro-Diels-Alder reaction: Hopf, H.; Theurig, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1099. Hopf, H.; Theurig, M.; Jones, P. G.; Bubenitschek, P. Liebigs Ann. 1996, 1301. Bunnage, M. E.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1110. Bunnage, M. E.; Nicolaou, K. C. Chem. Eur. J. 1997, 3, 187. Review: Maier, M. E. Synlett 1995, 13.
26. Formation of enediynes from stable precursors by reductive elimination: Myers, A. G.; Dragovich, P. S. J. Am. Chem. Soc. 1992, 114, 5859. By acid- or base-induced elimination of alcohols: Petasis, N. A.; Teets, K. A. Tetrahedron Lett. 1993, 34, 805. Yoshimatsu, M.; Yamada, H.; Shimizu, H.; Kataoka, T. J. Chem. Soc., Chem. Commun. 1994, 2107. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Grierson, D. S. Synlett 1993, 20. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Riche, C.; Chiaroni, A.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Shibuya, M.; Sakai, Y.; Naoe, Y. Tetrahedron Lett. 1995, 36, 897. Iida, K.; Hirama, M. J. Am. Chem. Soc. 1995, 117, 8875. Kawata, S.; Yoshimura, F.; Irie, J.; Ehara, H.; Hirama, M. Synlett 1997, 250. Wang, J.; De Clercq, P. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1749. Takahashi, T.; Tanaka, H.; Matsuda, A.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Tetrahedron Lett. 1996, 37, 2433. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1996, 35, 1835. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 1524. By the Corey-Winter reagent: Semmelhack, M. F.; Gallagher, J.; Tetrahedron Lett. 1993, 34, 4121. Semmelhack, M. F.; Gallagher, J. J.; Ding, W.-D.; Krishnamurthy, G.; Babine, R.; Ellestad, G. A. J. Org. Chem. 1994, 59, 4357. By benzylic oxidation: Huber, R. S.; Jones, G. B. Tetrahedron Lett. 1994, 35, 2655. Maier, M. E.; Greiner, B. Liebigs Ann. Chem. 1992, 855. By the Norrish type-II reaction: Nuss, J. M.; Murphy, M. M. Tetrahedron Lett. 1994, 35, 37. By the Diels-Alder or retro-Diels-Alder reaction: Hopf, H.; Theurig, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1099. Hopf, H.; Theurig, M.; Jones, P. G.; Bubenitschek, P. Liebigs Ann. 1996, 1301. Bunnage, M. E.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1110. Bunnage, M. E.; Nicolaou, K. C. Chem. Eur. J. 1997, 3, 187. Review: Maier, M. E. Synlett 1995, 13.
27. Formation of enediynes from stable precursors by reductive elimination: Myers, A. G.; Dragovich, P. S. J. Am. Chem. Soc. 1992, 114, 5859. By acid- or base-induced elimination of alcohols: Petasis, N. A.; Teets, K. A. Tetrahedron Lett. 1993, 34, 805. Yoshimatsu, M.; Yamada, H.; Shimizu, H.; Kataoka, T. J. Chem. Soc., Chem. Commun. 1994, 2107. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Grierson, D. S. Synlett 1993, 20. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Riche, C.; Chiaroni, A.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Shibuya, M.; Sakai, Y.; Naoe, Y. Tetrahedron Lett. 1995, 36, 897. Iida, K.; Hirama, M. J. Am. Chem. Soc. 1995, 117, 8875. Kawata, S.; Yoshimura, F.; Irie, J.; Ehara, H.; Hirama, M. Synlett 1997, 250. Wang, J.; De Clercq, P. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1749. Takahashi, T.; Tanaka, H.; Matsuda, A.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Tetrahedron Lett. 1996, 37, 2433. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1996, 35, 1835. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 1524. By the Corey-Winter reagent: Semmelhack, M. F.; Gallagher, J.; Tetrahedron Lett. 1993, 34, 4121. Semmelhack, M. F.; Gallagher, J. J.; Ding, W.-D.; Krishnamurthy, G.; Babine, R.; Ellestad, G. A. J. Org. Chem. 1994, 59, 4357. By benzylic oxidation: Huber, R. S.; Jones, G. B. Tetrahedron Lett. 1994, 35, 2655. Maier, M. E.; Greiner, B. Liebigs Ann. Chem. 1992, 855. By the Norrish type-II reaction: Nuss, J. M.; Murphy, M. M. Tetrahedron Lett. 1994, 35, 37. By the Diels-Alder or retro-Diels-Alder reaction: Hopf, H.; Theurig, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1099. Hopf, H.; Theurig, M.; Jones, P. G.; Bubenitschek, P. Liebigs Ann. 1996, 1301. Bunnage, M. E.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1110. Bunnage, M. E.; Nicolaou, K. C. Chem. Eur. J. 1997, 3, 187. Review: Maier, M. E. Synlett 1995, 13.
28. Formation of enediynes from stable precursors by reductive elimination: Myers, A. G.; Dragovich, P. S. J. Am. Chem. Soc. 1992, 114, 5859. By acid- or base-induced elimination of alcohols: Petasis, N. A.; Teets, K. A. Tetrahedron Lett. 1993, 34, 805. Yoshimatsu, M.; Yamada, H.; Shimizu, H.; Kataoka, T. J. Chem. Soc., Chem. Commun. 1994, 2107. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Grierson, D. S. Synlett 1993, 20. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Riche, C.; Chiaroni, A.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Shibuya, M.; Sakai, Y.; Naoe, Y. Tetrahedron Lett. 1995, 36, 897. Iida, K.; Hirama, M. J. Am. Chem. Soc. 1995, 117, 8875. Kawata, S.; Yoshimura, F.; Irie, J.; Ehara, H.; Hirama, M. Synlett 1997, 250. Wang, J.; De Clercq, P. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1749. Takahashi, T.; Tanaka, H.; Matsuda, A.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Tetrahedron Lett. 1996, 37, 2433. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1996, 35, 1835. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 1524. By the Corey-Winter reagent: Semmelhack, M. F.; Gallagher, J.; Tetrahedron Lett. 1993, 34, 4121. Semmelhack, M. F.; Gallagher, J. J.; Ding, W.-D.; Krishnamurthy, G.; Babine, R.; Ellestad, G. A. J. Org. Chem. 1994, 59, 4357. By benzylic oxidation: Huber, R. S.; Jones, G. B. Tetrahedron Lett. 1994, 35, 2655. Maier, M. E.; Greiner, B. Liebigs Ann. Chem. 1992, 855. By the Norrish type-II reaction: Nuss, J. M.; Murphy, M. M. Tetrahedron Lett. 1994, 35, 37. By the Diels-Alder or retro-Diels-Alder reaction: Hopf, H.; Theurig, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1099. Hopf, H.; Theurig, M.; Jones, P. G.; Bubenitschek, P. Liebigs Ann. 1996, 1301. Bunnage, M. E.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1110. Bunnage, M. E.; Nicolaou, K. C. Chem. Eur. J. 1997, 3, 187. Review: Maier, M. E. Synlett 1995, 13.
29. Formation of enediynes from stable precursors by reductive elimination: Myers, A. G.; Dragovich, P. S. J. Am. Chem. Soc. 1992, 114, 5859. By acid- or base-induced elimination of alcohols: Petasis, N. A.; Teets, K. A. Tetrahedron Lett. 1993, 34, 805. Yoshimatsu, M.; Yamada, H.; Shimizu, H.; Kataoka, T. J. Chem. Soc., Chem. Commun. 1994, 2107. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Grierson, D. S. Synlett 1993, 20. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Riche, C.; Chiaroni, A.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Shibuya, M.; Sakai, Y.; Naoe, Y. Tetrahedron Lett. 1995, 36, 897. Iida, K.; Hirama, M. J. Am. Chem. Soc. 1995, 117, 8875. Kawata, S.; Yoshimura, F.; Irie, J.; Ehara, H.; Hirama, M. Synlett 1997, 250. Wang, J.; De Clercq, P. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1749. Takahashi, T.; Tanaka, H.; Matsuda, A.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Tetrahedron Lett. 1996, 37, 2433. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1996, 35, 1835. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 1524. By the Corey-Winter reagent: Semmelhack, M. F.; Gallagher, J.; Tetrahedron Lett. 1993, 34, 4121. Semmelhack, M. F.; Gallagher, J. J.; Ding, W.-D.; Krishnamurthy, G.; Babine, R.; Ellestad, G. A. J. Org. Chem. 1994, 59, 4357. By benzylic oxidation: Huber, R. S.; Jones, G. B. Tetrahedron Lett. 1994, 35, 2655. Maier, M. E.; Greiner, B. Liebigs Ann. Chem. 1992, 855. By the Norrish type-II reaction: Nuss, J. M.; Murphy, M. M. Tetrahedron Lett. 1994, 35, 37. By the Diels-Alder or retro-Diels-Alder reaction: Hopf, H.; Theurig, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1099. Hopf, H.; Theurig, M.; Jones, P. G.; Bubenitschek, P. Liebigs Ann. 1996, 1301. Bunnage, M. E.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1110. Bunnage, M. E.; Nicolaou, K. C. Chem. Eur. J. 1997, 3, 187. Review: Maier, M. E. Synlett 1995, 13.
30. Formation of enediynes from stable precursors by reductive elimination: Myers, A. G.; Dragovich, P. S. J. Am. Chem. Soc. 1992, 114, 5859. By acid- or base-induced elimination of alcohols: Petasis, N. A.; Teets, K. A. Tetrahedron Lett. 1993, 34, 805. Yoshimatsu, M.; Yamada, H.; Shimizu, H.; Kataoka, T. J. Chem. Soc., Chem. Commun. 1994, 2107. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Grierson, D. S. Synlett 1993, 20. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Riche, C.; Chiaroni, A.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Shibuya, M.; Sakai, Y.; Naoe, Y. Tetrahedron Lett. 1995, 36, 897. Iida, K.; Hirama, M. J. Am. Chem. Soc. 1995, 117, 8875. Kawata, S.; Yoshimura, F.; Irie, J.; Ehara, H.; Hirama, M. Synlett 1997, 250. Wang, J.; De Clercq, P. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1749. Takahashi, T.; Tanaka, H.; Matsuda, A.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Tetrahedron Lett. 1996, 37, 2433. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1996, 35, 1835. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 1524. By the Corey-Winter reagent: Semmelhack, M. F.; Gallagher, J.; Tetrahedron Lett. 1993, 34, 4121. Semmelhack, M. F.; Gallagher, J. J.; Ding, W.-D.; Krishnamurthy, G.; Babine, R.; Ellestad, G. A. J. Org. Chem. 1994, 59, 4357. By benzylic oxidation: Huber, R. S.; Jones, G. B. Tetrahedron Lett. 1994, 35, 2655. Maier, M. E.; Greiner, B. Liebigs Ann. Chem. 1992, 855. By the Norrish type-II reaction: Nuss, J. M.; Murphy, M. M. Tetrahedron Lett. 1994, 35, 37. By the Diels-Alder or retro-Diels-Alder reaction: Hopf, H.; Theurig, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1099. Hopf, H.; Theurig, M.; Jones, P. G.; Bubenitschek, P. Liebigs Ann. 1996, 1301. Bunnage, M. E.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1110. Bunnage, M. E.; Nicolaou, K. C. Chem. Eur. J. 1997, 3, 187. Review: Maier, M. E. Synlett 1995, 13.
31. Formation of enediynes from stable precursors by reductive elimination: Myers, A. G.; Dragovich, P. S. J. Am. Chem. Soc. 1992, 114, 5859. By acid- or base-induced elimination of alcohols: Petasis, N. A.; Teets, K. A. Tetrahedron Lett. 1993, 34, 805. Yoshimatsu, M.; Yamada, H.; Shimizu, H.; Kataoka, T. J. Chem. Soc., Chem. Commun. 1994, 2107. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Grierson, D. S. Synlett 1993, 20. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Riche, C.; Chiaroni, A.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Shibuya, M.; Sakai, Y.; Naoe, Y. Tetrahedron Lett. 1995, 36, 897. Iida, K.; Hirama, M. J. Am. Chem. Soc. 1995, 117, 8875. Kawata, S.; Yoshimura, F.; Irie, J.; Ehara, H.; Hirama, M. Synlett 1997, 250. Wang, J.; De Clercq, P. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1749. Takahashi, T.; Tanaka, H.; Matsuda, A.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Tetrahedron Lett. 1996, 37, 2433. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1996, 35, 1835. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 1524. By the Corey-Winter reagent: Semmelhack, M. F.; Gallagher, J.; Tetrahedron Lett. 1993, 34, 4121. Semmelhack, M. F.; Gallagher, J. J.; Ding, W.-D.; Krishnamurthy, G.; Babine, R.; Ellestad, G. A. J. Org. Chem. 1994, 59, 4357. By benzylic oxidation: Huber, R. S.; Jones, G. B. Tetrahedron Lett. 1994, 35, 2655. Maier, M. E.; Greiner, B. Liebigs Ann. Chem. 1992, 855. By the Norrish type-II reaction: Nuss, J. M.; Murphy, M. M. Tetrahedron Lett. 1994, 35, 37. By the Diels-Alder or retro-Diels-Alder reaction: Hopf, H.; Theurig, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1099. Hopf, H.; Theurig, M.; Jones, P. G.; Bubenitschek, P. Liebigs Ann. 1996, 1301. Bunnage, M. E.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1110. Bunnage, M. E.; Nicolaou, K. C. Chem. Eur. J. 1997, 3, 187. Review: Maier, M. E. Synlett 1995, 13.
32. Formation of enediynes from stable precursors by reductive elimination: Myers, A. G.; Dragovich, P. S. J. Am. Chem. Soc. 1992, 114, 5859. By acid- or base-induced elimination of alcohols: Petasis, N. A.; Teets, K. A. Tetrahedron Lett. 1993, 34, 805. Yoshimatsu, M.; Yamada, H.; Shimizu, H.; Kataoka, T. J. Chem. Soc., Chem. Commun. 1994, 2107. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Grierson, D. S. Synlett 1993, 20. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Riche, C.; Chiaroni, A.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Shibuya, M.; Sakai, Y.; Naoe, Y. Tetrahedron Lett. 1995, 36, 897. Iida, K.; Hirama, M. J. Am. Chem. Soc. 1995, 117, 8875. Kawata, S.; Yoshimura, F.; Irie, J.; Ehara, H.; Hirama, M. Synlett 1997, 250. Wang, J.; De Clercq, P. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1749. Takahashi, T.; Tanaka, H.; Matsuda, A.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Tetrahedron Lett. 1996, 37, 2433. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1996, 35, 1835. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 1524. By the Corey-Winter reagent: Semmelhack, M. F.; Gallagher, J.; Tetrahedron Lett. 1993, 34, 4121. Semmelhack, M. F.; Gallagher, J. J.; Ding, W.-D.; Krishnamurthy, G.; Babine, R.; Ellestad, G. A. J. Org. Chem. 1994, 59, 4357. By benzylic oxidation: Huber, R. S.; Jones, G. B. Tetrahedron Lett. 1994, 35, 2655. Maier, M. E.; Greiner, B. Liebigs Ann. Chem. 1992, 855. By the Norrish type-II reaction: Nuss, J. M.; Murphy, M. M. Tetrahedron Lett. 1994, 35, 37. By the Diels-Alder or retro-Diels-Alder reaction: Hopf, H.; Theurig, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1099. Hopf, H.; Theurig, M.; Jones, P. G.; Bubenitschek, P. Liebigs Ann. 1996, 1301. Bunnage, M. E.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1110. Bunnage, M. E.; Nicolaou, K. C. Chem. Eur. J. 1997, 3, 187. Review: Maier, M. E. Synlett 1995, 13.
33. Formation of enediynes from stable precursors by reductive elimination: Myers, A. G.; Dragovich, P. S. J. Am. Chem. Soc. 1992, 114, 5859. By acid- or base-induced elimination of alcohols: Petasis, N. A.; Teets, K. A. Tetrahedron Lett. 1993, 34, 805. Yoshimatsu, M.; Yamada, H.; Shimizu, H.; Kataoka, T. J. Chem. Soc., Chem. Commun. 1994, 2107. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Grierson, D. S. Synlett 1993, 20. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Riche, C.; Chiaroni, A.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Shibuya, M.; Sakai, Y.; Naoe, Y. Tetrahedron Lett. 1995, 36, 897. Iida, K.; Hirama, M. J. Am. Chem. Soc. 1995, 117, 8875. Kawata, S.; Yoshimura, F.; Irie, J.; Ehara, H.; Hirama, M. Synlett 1997, 250. Wang, J.; De Clercq, P. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1749. Takahashi, T.; Tanaka, H.; Matsuda, A.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Tetrahedron Lett. 1996, 37, 2433. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1996, 35, 1835. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 1524. By the Corey-Winter reagent: Semmelhack, M. F.; Gallagher, J.; Tetrahedron Lett. 1993, 34, 4121. Semmelhack, M. F.; Gallagher, J. J.; Ding, W.-D.; Krishnamurthy, G.; Babine, R.; Ellestad, G. A. J. Org. Chem. 1994, 59, 4357. By benzylic oxidation: Huber, R. S.; Jones, G. B. Tetrahedron Lett. 1994, 35, 2655. Maier, M. E.; Greiner, B. Liebigs Ann. Chem. 1992, 855. By the Norrish type-II reaction: Nuss, J. M.; Murphy, M. M. Tetrahedron Lett. 1994, 35, 37. By the Diels-Alder or retro-Diels-Alder reaction: Hopf, H.; Theurig, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1099. Hopf, H.; Theurig, M.; Jones, P. G.; Bubenitschek, P. Liebigs Ann. 1996, 1301. Bunnage, M. E.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1110. Bunnage, M. E.; Nicolaou, K. C. Chem. Eur. J. 1997, 3, 187. Review: Maier, M. E. Synlett 1995, 13.
34. Formation of enediynes from stable precursors by reductive elimination: Myers, A. G.; Dragovich, P. S. J. Am. Chem. Soc. 1992, 114, 5859. By acid- or base-induced elimination of alcohols: Petasis, N. A.; Teets, K. A. Tetrahedron Lett. 1993, 34, 805. Yoshimatsu, M.; Yamada, H.; Shimizu, H.; Kataoka, T. J. Chem. Soc., Chem. Commun. 1994, 2107. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Grierson, D. S. Synlett 1993, 20. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Riche, C.; Chiaroni, A.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Shibuya, M.; Sakai, Y.; Naoe, Y. Tetrahedron Lett. 1995, 36, 897. Iida, K.; Hirama, M. J. Am. Chem. Soc. 1995, 117, 8875. Kawata, S.; Yoshimura, F.; Irie, J.; Ehara, H.; Hirama, M. Synlett 1997, 250. Wang, J.; De Clercq, P. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1749. Takahashi, T.; Tanaka, H.; Matsuda, A.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Tetrahedron Lett. 1996, 37, 2433. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1996, 35, 1835. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 1524. By the Corey-Winter reagent: Semmelhack, M. F.; Gallagher, J.; Tetrahedron Lett. 1993, 34, 4121. Semmelhack, M. F.; Gallagher, J. J.; Ding, W.-D.; Krishnamurthy, G.; Babine, R.; Ellestad, G. A. J. Org. Chem. 1994, 59, 4357. By benzylic oxidation: Huber, R. S.; Jones, G. B. Tetrahedron Lett. 1994, 35, 2655. Maier, M. E.; Greiner, B. Liebigs Ann. Chem. 1992, 855. By the Norrish type-II reaction: Nuss, J. M.; Murphy, M. M. Tetrahedron Lett. 1994, 35, 37. By the Diels-Alder or retro-Diels-Alder reaction: Hopf, H.; Theurig, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1099. Hopf, H.; Theurig, M.; Jones, P. G.; Bubenitschek, P. Liebigs Ann. 1996, 1301. Bunnage, M. E.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1110. Bunnage, M. E.; Nicolaou, K. C. Chem. Eur. J. 1997, 3, 187. Review: Maier, M. E. Synlett 1995, 13.
35. Formation of enediynes from stable precursors by reductive elimination: Myers, A. G.; Dragovich, P. S. J. Am. Chem. Soc. 1992, 114, 5859. By acid- or base-induced elimination of alcohols: Petasis, N. A.; Teets, K. A. Tetrahedron Lett. 1993, 34, 805. Yoshimatsu, M.; Yamada, H.; Shimizu, H.; Kataoka, T. J. Chem. Soc., Chem. Commun. 1994, 2107. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Grierson, D. S. Synlett 1993, 20. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Riche, C.; Chiaroni, A.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Shibuya, M.; Sakai, Y.; Naoe, Y. Tetrahedron Lett. 1995, 36, 897. Iida, K.; Hirama, M. J. Am. Chem. Soc. 1995, 117, 8875. Kawata, S.; Yoshimura, F.; Irie, J.; Ehara, H.; Hirama, M. Synlett 1997, 250. Wang, J.; De Clercq, P. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1749. Takahashi, T.; Tanaka, H.; Matsuda, A.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Tetrahedron Lett. 1996, 37, 2433. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1996, 35, 1835. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 1524. By the Corey-Winter reagent: Semmelhack, M. F.; Gallagher, J.; Tetrahedron Lett. 1993, 34, 4121. Semmelhack, M. F.; Gallagher, J. J.; Ding, W.-D.; Krishnamurthy, G.; Babine, R.; Ellestad, G. A. J. Org. Chem. 1994, 59, 4357. By benzylic oxidation: Huber, R. S.; Jones, G. B. Tetrahedron Lett. 1994, 35, 2655. Maier, M. E.; Greiner, B. Liebigs Ann. Chem. 1992, 855. By the Norrish type-II reaction: Nuss, J. M.; Murphy, M. M. Tetrahedron Lett. 1994, 35, 37. By the Diels-Alder or retro-Diels-Alder reaction: Hopf, H.; Theurig, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1099. Hopf, H.; Theurig, M.; Jones, P. G.; Bubenitschek, P. Liebigs Ann. 1996, 1301. Bunnage, M. E.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1110. Bunnage, M. E.; Nicolaou, K. C. Chem. Eur. J. 1997, 3, 187. Review: Maier, M. E. Synlett 1995, 13.
36. Formation of enediynes from stable precursors by reductive elimination: Myers, A. G.; Dragovich, P. S. J. Am. Chem. Soc. 1992, 114, 5859. By acid- or base-induced elimination of alcohols: Petasis, N. A.; Teets, K. A. Tetrahedron Lett. 1993, 34, 805. Yoshimatsu, M.; Yamada, H.; Shimizu, H.; Kataoka, T. J. Chem. Soc., Chem. Commun. 1994, 2107. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Grierson, D. S. Synlett 1993, 20. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Riche, C.; Chiaroni, A.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Shibuya, M.; Sakai, Y.; Naoe, Y. Tetrahedron Lett. 1995, 36, 897. Iida, K.; Hirama, M. J. Am. Chem. Soc. 1995, 117, 8875. Kawata, S.; Yoshimura, F.; Irie, J.; Ehara, H.; Hirama, M. Synlett 1997, 250. Wang, J.; De Clercq, P. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1749. Takahashi, T.; Tanaka, H.; Matsuda, A.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Tetrahedron Lett. 1996, 37, 2433. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1996, 35, 1835. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 1524. By the Corey-Winter reagent: Semmelhack, M. F.; Gallagher, J.; Tetrahedron Lett. 1993, 34, 4121. Semmelhack, M. F.; Gallagher, J. J.; Ding, W.-D.; Krishnamurthy, G.; Babine, R.; Ellestad, G. A. J. Org. Chem. 1994, 59, 4357. By benzylic oxidation: Huber, R. S.; Jones, G. B. Tetrahedron Lett. 1994, 35, 2655. Maier, M. E.; Greiner, B. Liebigs Ann. Chem. 1992, 855. By the Norrish type-II reaction: Nuss, J. M.; Murphy, M. M. Tetrahedron Lett. 1994, 35, 37. By the Diels-Alder or retro-Diels-Alder reaction: Hopf, H.; Theurig, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1099. Hopf, H.; Theurig, M.; Jones, P. G.; Bubenitschek, P. Liebigs Ann. 1996, 1301. Bunnage, M. E.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1110. Bunnage, M. E.; Nicolaou, K. C. Chem. Eur. J. 1997, 3, 187. Review: Maier, M. E. Synlett 1995, 13.
37. Formation of enediynes from stable precursors by reductive elimination: Myers, A. G.; Dragovich, P. S. J. Am. Chem. Soc. 1992, 114, 5859. By acid- or base-induced elimination of alcohols: Petasis, N. A.; Teets, K. A. Tetrahedron Lett. 1993, 34, 805. Yoshimatsu, M.; Yamada, H.; Shimizu, H.; Kataoka, T. J. Chem. Soc., Chem. Commun. 1994, 2107. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Grierson, D. S. Synlett 1993, 20. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Riche, C.; Chiaroni, A.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Shibuya, M.; Sakai, Y.; Naoe, Y. Tetrahedron Lett. 1995, 36, 897. Iida, K.; Hirama, M. J. Am. Chem. Soc. 1995, 117, 8875. Kawata, S.; Yoshimura, F.; Irie, J.; Ehara, H.; Hirama, M. Synlett 1997, 250. Wang, J.; De Clercq, P. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1749. Takahashi, T.; Tanaka, H.; Matsuda, A.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Tetrahedron Lett. 1996, 37, 2433. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1996, 35, 1835. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 1524. By the Corey-Winter reagent: Semmelhack, M. F.; Gallagher, J.; Tetrahedron Lett. 1993, 34, 4121. Semmelhack, M. F.; Gallagher, J. J.; Ding, W.-D.; Krishnamurthy, G.; Babine, R.; Ellestad, G. A. J. Org. Chem. 1994, 59, 4357. By benzylic oxidation: Huber, R. S.; Jones, G. B. Tetrahedron Lett. 1994, 35, 2655. Maier, M. E.; Greiner, B. Liebigs Ann. Chem. 1992, 855. By the Norrish type-II reaction: Nuss, J. M.; Murphy, M. M. Tetrahedron Lett. 1994, 35, 37. By the Diels-Alder or retro-Diels-Alder reaction: Hopf, H.; Theurig, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1099. Hopf, H.; Theurig, M.; Jones, P. G.; Bubenitschek, P. Liebigs Ann. 1996, 1301. Bunnage, M. E.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1110. Bunnage, M. E.; Nicolaou, K. C. Chem. Eur. J. 1997, 3, 187. Review: Maier, M. E. Synlett 1995, 13.
38. Formation of enediynes from stable precursors by reductive elimination: Myers, A. G.; Dragovich, P. S. J. Am. Chem. Soc. 1992, 114, 5859. By acid- or base-induced elimination of alcohols: Petasis, N. A.; Teets, K. A. Tetrahedron Lett. 1993, 34, 805. Yoshimatsu, M.; Yamada, H.; Shimizu, H.; Kataoka, T. J. Chem. Soc., Chem. Commun. 1994, 2107. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Grierson, D. S. Synlett 1993, 20. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Riche, C.; Chiaroni, A.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Shibuya, M.; Sakai, Y.; Naoe, Y. Tetrahedron Lett. 1995, 36, 897. Iida, K.; Hirama, M. J. Am. Chem. Soc. 1995, 117, 8875. Kawata, S.; Yoshimura, F.; Irie, J.; Ehara, H.; Hirama, M. Synlett 1997, 250. Wang, J.; De Clercq, P. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1749. Takahashi, T.; Tanaka, H.; Matsuda, A.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Tetrahedron Lett. 1996, 37, 2433. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1996, 35, 1835. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 1524. By the Corey-Winter reagent: Semmelhack, M. F.; Gallagher, J.; Tetrahedron Lett. 1993, 34, 4121. Semmelhack, M. F.; Gallagher, J. J.; Ding, W.-D.; Krishnamurthy, G.; Babine, R.; Ellestad, G. A. J. Org. Chem. 1994, 59, 4357. By benzylic oxidation: Huber, R. S.; Jones, G. B. Tetrahedron Lett. 1994, 35, 2655. Maier, M. E.; Greiner, B. Liebigs Ann. Chem. 1992, 855. By the Norrish type-II reaction: Nuss, J. M.; Murphy, M. M. Tetrahedron Lett. 1994, 35, 37. By the Diels-Alder or retro-Diels-Alder reaction: Hopf, H.; Theurig, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1099. Hopf, H.; Theurig, M.; Jones, P. G.; Bubenitschek, P. Liebigs Ann. 1996, 1301. Bunnage, M. E.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1110. Bunnage, M. E.; Nicolaou, K. C. Chem. Eur. J. 1997, 3, 187. Review: Maier, M. E. Synlett 1995, 13.
39. Formation of enediynes from stable precursors by reductive elimination: Myers, A. G.; Dragovich, P. S. J. Am. Chem. Soc. 1992, 114, 5859. By acid- or base-induced elimination of alcohols: Petasis, N. A.; Teets, K. A. Tetrahedron Lett. 1993, 34, 805. Yoshimatsu, M.; Yamada, H.; Shimizu, H.; Kataoka, T. J. Chem. Soc., Chem. Commun. 1994, 2107. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Grierson, D. S. Synlett 1993, 20. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Riche, C.; Chiaroni, A.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Shibuya, M.; Sakai, Y.; Naoe, Y. Tetrahedron Lett. 1995, 36, 897. Iida, K.; Hirama, M. J. Am. Chem. Soc. 1995, 117, 8875. Kawata, S.; Yoshimura, F.; Irie, J.; Ehara, H.; Hirama, M. Synlett 1997, 250. Wang, J.; De Clercq, P. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1749. Takahashi, T.; Tanaka, H.; Matsuda, A.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Tetrahedron Lett. 1996, 37, 2433. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1996, 35, 1835. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 1524. By the Corey-Winter reagent: Semmelhack, M. F.; Gallagher, J.; Tetrahedron Lett. 1993, 34, 4121. Semmelhack, M. F.; Gallagher, J. J.; Ding, W.-D.; Krishnamurthy, G.; Babine, R.; Ellestad, G. A. J. Org. Chem. 1994, 59, 4357. By benzylic oxidation: Huber, R. S.; Jones, G. B. Tetrahedron Lett. 1994, 35, 2655. Maier, M. E.; Greiner, B. Liebigs Ann. Chem. 1992, 855. By the Norrish type-II reaction: Nuss, J. M.; Murphy, M. M. Tetrahedron Lett. 1994, 35, 37. By the Diels-Alder or retro-Diels-Alder reaction: Hopf, H.; Theurig, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1099. Hopf, H.; Theurig, M.; Jones, P. G.; Bubenitschek, P. Liebigs Ann. 1996, 1301. Bunnage, M. E.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1110. Bunnage, M. E.; Nicolaou, K. C. Chem. Eur. J. 1997, 3, 187. Review: Maier, M. E. Synlett 1995, 13.
40. Formation of enediynes from stable precursors by reductive elimination: Myers, A. G.; Dragovich, P. S. J. Am. Chem. Soc. 1992, 114, 5859. By acid- or base-induced elimination of alcohols: Petasis, N. A.; Teets, K. A. Tetrahedron Lett. 1993, 34, 805. Yoshimatsu, M.; Yamada, H.; Shimizu, H.; Kataoka, T. J. Chem. Soc., Chem. Commun. 1994, 2107. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Grierson, D. S. Synlett 1993, 20. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Riche, C.; Chiaroni, A.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Shibuya, M.; Sakai, Y.; Naoe, Y. Tetrahedron Lett. 1995, 36, 897. Iida, K.; Hirama, M. J. Am. Chem. Soc. 1995, 117, 8875. Kawata, S.; Yoshimura, F.; Irie, J.; Ehara, H.; Hirama, M. Synlett 1997, 250. Wang, J.; De Clercq, P. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1749. Takahashi, T.; Tanaka, H.; Matsuda, A.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Tetrahedron Lett. 1996, 37, 2433. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1996, 35, 1835. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 1524. By the Corey-Winter reagent: Semmelhack, M. F.; Gallagher, J.; Tetrahedron Lett. 1993, 34, 4121. Semmelhack, M. F.; Gallagher, J. J.; Ding, W.-D.; Krishnamurthy, G.; Babine, R.; Ellestad, G. A. J. Org. Chem. 1994, 59, 4357. By benzylic oxidation: Huber, R. S.; Jones, G. B. Tetrahedron Lett. 1994, 35, 2655. Maier, M. E.; Greiner, B. Liebigs Ann. Chem. 1992, 855. By the Norrish type-II reaction: Nuss, J. M.; Murphy, M. M. Tetrahedron Lett. 1994, 35, 37. By the Diels-Alder or retro-Diels-Alder reaction: Hopf, H.; Theurig, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1099. Hopf, H.; Theurig, M.; Jones, P. G.; Bubenitschek, P. Liebigs Ann. 1996, 1301. Bunnage, M. E.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1110. Bunnage, M. E.; Nicolaou, K. C. Chem. Eur. J. 1997, 3, 187. Review: Maier, M. E. Synlett 1995, 13.
41. Formation of enediynes from stable precursors by reductive elimination: Myers, A. G.; Dragovich, P. S. J. Am. Chem. Soc. 1992, 114, 5859. By acid- or base-induced elimination of alcohols: Petasis, N. A.; Teets, K. A. Tetrahedron Lett. 1993, 34, 805. Yoshimatsu, M.; Yamada, H.; Shimizu, H.; Kataoka, T. J. Chem. Soc., Chem. Commun. 1994, 2107. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Grierson, D. S. Synlett 1993, 20. Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Riche, C.; Chiaroni, A.; Grierson, D. S. Tetrahedron 1994, 50, 1469. Shibuya, M.; Sakai, Y.; Naoe, Y. Tetrahedron Lett. 1995, 36, 897. Iida, K.; Hirama, M. J. Am. Chem. Soc. 1995, 117, 8875. Kawata, S.; Yoshimura, F.; Irie, J.; Ehara, H.; Hirama, M. Synlett 1997, 250. Wang, J.; De Clercq, P. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1749. Takahashi, T.; Tanaka, H.; Matsuda, A.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Tetrahedron Lett. 1996, 37, 2433. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1996, 35, 1835. Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 1524. By the Corey-Winter reagent: Semmelhack, M. F.; Gallagher, J.; Tetrahedron Lett. 1993, 34, 4121. Semmelhack, M. F.; Gallagher, J. J.; Ding, W.-D.; Krishnamurthy, G.; Babine, R.; Ellestad, G. A. J. Org. Chem. 1994, 59, 4357. By benzylic oxidation: Huber, R. S.; Jones, G. B. Tetrahedron Lett. 1994, 35, 2655. Maier, M. E.; Greiner, B. Liebigs Ann. Chem. 1992, 855. By the Norrish type-II reaction: Nuss, J. M.; Murphy, M. M. Tetrahedron Lett. 1994, 35, 37. By the Diels-Alder or retro-Diels-Alder reaction: Hopf, H.; Theurig, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1099. Hopf, H.; Theurig, M.; Jones, P. G.; Bubenitschek, P. Liebigs Ann. 1996, 1301. Bunnage, M. E.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1110. Bunnage, M. E.; Nicolaou, K. C. Chem. Eur. J. 1997, 3, 187. Review: Maier, M. E. Synlett 1995, 13.
42. For DNA-mediated acid catalysis, see: Lamm, G.; Wong, L.; Pack, G. R. J. Am. Chem. Soc. 1996, 118, 3325 and references therein.
43. Logically, acidic pHs should favor the conversion of 1 into 2b, and we observed a slightly increased potency of DNA cleavage by 1 when the pH was changed from 8.5 to 6.0. However, due to substantial decomposition of the DNA samples from two commercial sources in the acidic pHs, the observed pH effect on DNA cleavage of 1 is not very significant or convincing.
44. Dai, W.-M.; Wu, J. preliminary results for acyclic substrates were presented at the AFMC International Medicinal Chemistry Symposium, July 27-Aug 1, 1997, Seoul, Korea; Abstract OA-2.