The bis(enol triflate) route to dienediyne models of the biradical forming and DNA-cleaving natural product neocarzinostatin chromophore

Synlett

Volumn , Issue 6, 1999, Pages 657-679

  Brückner, Reinhard ^a   Suffert, Jean ^b  

^a UNIVERSITY OF FREIBURG   (Germany)

^b Laboratoire de Pharmacochimie   (France)

Author keywords

C,C coupling; Dienediynes; Enediyne antibiotics; Enol triflate; Neocarzinostatin

Indexed keywords

ALKYNE; ZINOSTATIN;

AROMATIZATION; ARTICLE; CHEMICAL STRUCTURE; CHROMATOPHORE; CRYSTAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SOLID STATE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0041815722     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2699     Document Type: Article

References (138)

1. Isolation and purification of neocarzinostatin: J. Shoji, J. Antibiot. 1961, 14, 27-33; N. Ishida, M. Miyazaki, K. Kumagai, M. Rikimaru, J. Antibiot. 1965, 18, 68-76. Gross composition of neocarzinostatin: M. A. Napier, B. Holmquist, D. J. Strydom, I. H. Goldberg, Biochem. Biophys. Res. Comm. 1979, 89, 635-642; Y. Koide, F. Ishi, K. Hasuda, Y. Koyama, K. Edo, S. Katamine, F. Kitame, N. Ishida, J. Antibiot. 1980, 33, 342-346. Biology of neocarzinostatin: Goldberg; I. H. Acc. Chem. Res. 1991, 24, 191-198; Saito, I. Toxicol. Lett. 1993, 67, 3-15. H. Maeda, K. Edo, N. Ishida, Neocarzinostatin, Springer, Tokyo, 1997. Chemistry of neocarzinostatin and analogs thereof: Hirama, M. in Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products, Vol. 2 (G. Lukacs, Ed.), Springer, Berlin, 1993, 293-329; Hirama, M. J. Synth. Org. Chem. Jpn. 1994, 52, 980-991; J. Suffert, R. Brückner, Lettre des Sciences Chimiques, février-avril 1996, 25-29; H. Lhermitte, D. Grierson, Contemp. Org. Synth. 1996, 3, 93-124; J. W. Grissom, G. U. Gunawardena, D, Klingberg, D. Huang, Tetrahedron 1996, 52, 6453-6518.
2. Isolation and purification of neocarzinostatin: J. Shoji, J. Antibiot. 1961, 14, 27-33; N. Ishida, M. Miyazaki, K. Kumagai, M. Rikimaru, J. Antibiot. 1965, 18, 68-76. Gross composition of neocarzinostatin: M. A. Napier, B. Holmquist, D. J. Strydom, I. H. Goldberg, Biochem. Biophys. Res. Comm. 1979, 89, 635-642; Y. Koide, F. Ishi, K. Hasuda, Y. Koyama, K. Edo, S. Katamine, F. Kitame, N. Ishida, J. Antibiot. 1980, 33, 342-346. Biology of neocarzinostatin: Goldberg; I. H. Acc. Chem. Res. 1991, 24, 191-198; Saito, I. Toxicol. Lett. 1993, 67, 3-15. H. Maeda, K. Edo, N. Ishida, Neocarzinostatin, Springer, Tokyo, 1997. Chemistry of neocarzinostatin and analogs thereof: Hirama, M. in Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products, Vol. 2 (G. Lukacs, Ed.), Springer, Berlin, 1993, 293-329; Hirama, M. J. Synth. Org. Chem. Jpn. 1994, 52, 980-991; J. Suffert, R. Brückner, Lettre des Sciences Chimiques, février-avril 1996, 25-29; H. Lhermitte, D. Grierson, Contemp. Org. Synth. 1996, 3, 93-124; J. W. Grissom, G. U. Gunawardena, D, Klingberg, D. Huang, Tetrahedron 1996, 52, 6453-6518.
3. Isolation and purification of neocarzinostatin: J. Shoji, J. Antibiot. 1961, 14, 27-33; N. Ishida, M. Miyazaki, K. Kumagai, M. Rikimaru, J. Antibiot. 1965, 18, 68-76. Gross composition of neocarzinostatin: M. A. Napier, B. Holmquist, D. J. Strydom, I. H. Goldberg, Biochem. Biophys. Res. Comm. 1979, 89, 635-642; Y. Koide, F. Ishi, K. Hasuda, Y. Koyama, K. Edo, S. Katamine, F. Kitame, N. Ishida, J. Antibiot. 1980, 33, 342-346. Biology of neocarzinostatin: Goldberg; I. H. Acc. Chem. Res. 1991, 24, 191-198; Saito, I. Toxicol. Lett. 1993, 67, 3-15. H. Maeda, K. Edo, N. Ishida, Neocarzinostatin, Springer, Tokyo, 1997. Chemistry of neocarzinostatin and analogs thereof: Hirama, M. in Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products, Vol. 2 (G. Lukacs, Ed.), Springer, Berlin, 1993, 293-329; Hirama, M. J. Synth. Org. Chem. Jpn. 1994, 52, 980-991; J. Suffert, R. Brückner, Lettre des Sciences Chimiques, février-avril 1996, 25-29; H. Lhermitte, D. Grierson, Contemp. Org. Synth. 1996, 3, 93-124; J. W. Grissom, G. U. Gunawardena, D, Klingberg, D. Huang, Tetrahedron 1996, 52, 6453-6518.
4. Isolation and purification of neocarzinostatin: J. Shoji, J. Antibiot. 1961, 14, 27-33; N. Ishida, M. Miyazaki, K. Kumagai, M. Rikimaru, J. Antibiot. 1965, 18, 68-76. Gross composition of neocarzinostatin: M. A. Napier, B. Holmquist, D. J. Strydom, I. H. Goldberg, Biochem. Biophys. Res. Comm. 1979, 89, 635-642; Y. Koide, F. Ishi, K. Hasuda, Y. Koyama, K. Edo, S. Katamine, F. Kitame, N. Ishida, J. Antibiot. 1980, 33, 342-346. Biology of neocarzinostatin: Goldberg; I. H. Acc. Chem. Res. 1991, 24, 191-198; Saito, I. Toxicol. Lett. 1993, 67, 3-15. H. Maeda, K. Edo, N. Ishida, Neocarzinostatin, Springer, Tokyo, 1997. Chemistry of neocarzinostatin and analogs thereof: Hirama, M. in Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products, Vol. 2 (G. Lukacs, Ed.), Springer, Berlin, 1993, 293-329; Hirama, M. J. Synth. Org. Chem. Jpn. 1994, 52, 980-991; J. Suffert, R. Brückner, Lettre des Sciences Chimiques, février-avril 1996, 25-29; H. Lhermitte, D. Grierson, Contemp. Org. Synth. 1996, 3, 93-124; J. W. Grissom, G. U. Gunawardena, D, Klingberg, D. Huang, Tetrahedron 1996, 52, 6453-6518.
5. Isolation and purification of neocarzinostatin: J. Shoji, J. Antibiot. 1961, 14, 27-33; N. Ishida, M. Miyazaki, K. Kumagai, M. Rikimaru, J. Antibiot. 1965, 18, 68-76. Gross composition of neocarzinostatin: M. A. Napier, B. Holmquist, D. J. Strydom, I. H. Goldberg, Biochem. Biophys. Res. Comm. 1979, 89, 635-642; Y. Koide, F. Ishi, K. Hasuda, Y. Koyama, K. Edo, S. Katamine, F. Kitame, N. Ishida, J. Antibiot. 1980, 33, 342-346. Biology of neocarzinostatin: Goldberg; I. H. Acc. Chem. Res. 1991, 24, 191-198; Saito, I. Toxicol. Lett. 1993, 67, 3-15. H. Maeda, K. Edo, N. Ishida, Neocarzinostatin, Springer, Tokyo, 1997. Chemistry of neocarzinostatin and analogs thereof: Hirama, M. in Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products, Vol. 2 (G. Lukacs, Ed.), Springer, Berlin, 1993, 293-329; Hirama, M. J. Synth. Org. Chem. Jpn. 1994, 52, 980-991; J. Suffert, R. Brückner, Lettre des Sciences Chimiques, février-avril 1996, 25-29; H. Lhermitte, D. Grierson, Contemp. Org. Synth. 1996, 3, 93-124; J. W. Grissom, G. U. Gunawardena, D, Klingberg, D. Huang, Tetrahedron 1996, 52, 6453-6518.
6. Isolation and purification of neocarzinostatin: J. Shoji, J. Antibiot. 1961, 14, 27-33; N. Ishida, M. Miyazaki, K. Kumagai, M. Rikimaru, J. Antibiot. 1965, 18, 68-76. Gross composition of neocarzinostatin: M. A. Napier, B. Holmquist, D. J. Strydom, I. H. Goldberg, Biochem. Biophys. Res. Comm. 1979, 89, 635-642; Y. Koide, F. Ishi, K. Hasuda, Y. Koyama, K. Edo, S. Katamine, F. Kitame, N. Ishida, J. Antibiot. 1980, 33, 342-346. Biology of neocarzinostatin: Goldberg; I. H. Acc. Chem. Res. 1991, 24, 191-198; Saito, I. Toxicol. Lett. 1993, 67, 3-15. H. Maeda, K. Edo, N. Ishida, Neocarzinostatin, Springer, Tokyo, 1997. Chemistry of neocarzinostatin and analogs thereof: Hirama, M. in Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products, Vol. 2 (G. Lukacs, Ed.), Springer, Berlin, 1993, 293-329; Hirama, M. J. Synth. Org. Chem. Jpn. 1994, 52, 980-991; J. Suffert, R. Brückner, Lettre des Sciences Chimiques, février-avril 1996, 25-29; H. Lhermitte, D. Grierson, Contemp. Org. Synth. 1996, 3, 93-124; J. W. Grissom, G. U. Gunawardena, D, Klingberg, D. Huang, Tetrahedron 1996, 52, 6453-6518.
7. Isolation and purification of neocarzinostatin: J. Shoji, J. Antibiot. 1961, 14, 27-33; N. Ishida, M. Miyazaki, K. Kumagai, M. Rikimaru, J. Antibiot. 1965, 18, 68-76. Gross composition of neocarzinostatin: M. A. Napier, B. Holmquist, D. J. Strydom, I. H. Goldberg, Biochem. Biophys. Res. Comm. 1979, 89, 635-642; Y. Koide, F. Ishi, K. Hasuda, Y. Koyama, K. Edo, S. Katamine, F. Kitame, N. Ishida, J. Antibiot. 1980, 33, 342-346. Biology of neocarzinostatin: Goldberg; I. H. Acc. Chem. Res. 1991, 24, 191-198; Saito, I. Toxicol. Lett. 1993, 67, 3-15. H. Maeda, K. Edo, N. Ishida, Neocarzinostatin, Springer, Tokyo, 1997. Chemistry of neocarzinostatin and analogs thereof: Hirama, M. in Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products, Vol. 2 (G. Lukacs, Ed.), Springer, Berlin, 1993, 293-329; Hirama, M. J. Synth. Org. Chem. Jpn. 1994, 52, 980-991; J. Suffert, R. Brückner, Lettre des Sciences Chimiques, février-avril 1996, 25-29; H. Lhermitte, D. Grierson, Contemp. Org. Synth. 1996, 3, 93-124; J. W. Grissom, G. U. Gunawardena, D, Klingberg, D. Huang, Tetrahedron 1996, 52, 6453-6518.
8. Isolation and purification of neocarzinostatin: J. Shoji, J. Antibiot. 1961, 14, 27-33; N. Ishida, M. Miyazaki, K. Kumagai, M. Rikimaru, J. Antibiot. 1965, 18, 68-76. Gross composition of neocarzinostatin: M. A. Napier, B. Holmquist, D. J. Strydom, I. H. Goldberg, Biochem. Biophys. Res. Comm. 1979, 89, 635-642; Y. Koide, F. Ishi, K. Hasuda, Y. Koyama, K. Edo, S. Katamine, F. Kitame, N. Ishida, J. Antibiot. 1980, 33, 342-346. Biology of neocarzinostatin: Goldberg; I. H. Acc. Chem. Res. 1991, 24, 191-198; Saito, I. Toxicol. Lett. 1993, 67, 3-15. H. Maeda, K. Edo, N. Ishida, Neocarzinostatin, Springer, Tokyo, 1997. Chemistry of neocarzinostatin and analogs thereof: Hirama, M. in Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products, Vol. 2 (G. Lukacs, Ed.), Springer, Berlin, 1993, 293-329; Hirama, M. J. Synth. Org. Chem. Jpn. 1994, 52, 980-991; J. Suffert, R. Brückner, Lettre des Sciences Chimiques, février-avril 1996, 25-29; H. Lhermitte, D. Grierson, Contemp. Org. Synth. 1996, 3, 93-124; J. W. Grissom, G. U. Gunawardena, D, Klingberg, D. Huang, Tetrahedron 1996, 52, 6453-6518.
9. Isolation and purification of neocarzinostatin: J. Shoji, J. Antibiot. 1961, 14, 27-33; N. Ishida, M. Miyazaki, K. Kumagai, M. Rikimaru, J. Antibiot. 1965, 18, 68-76. Gross composition of neocarzinostatin: M. A. Napier, B. Holmquist, D. J. Strydom, I. H. Goldberg, Biochem. Biophys. Res. Comm. 1979, 89, 635-642; Y. Koide, F. Ishi, K. Hasuda, Y. Koyama, K. Edo, S. Katamine, F. Kitame, N. Ishida, J. Antibiot. 1980, 33, 342-346. Biology of neocarzinostatin: Goldberg; I. H. Acc. Chem. Res. 1991, 24, 191-198; Saito, I. Toxicol. Lett. 1993, 67, 3-15. H. Maeda, K. Edo, N. Ishida, Neocarzinostatin, Springer, Tokyo, 1997. Chemistry of neocarzinostatin and analogs thereof: Hirama, M. in Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products, Vol. 2 (G. Lukacs, Ed.), Springer, Berlin, 1993, 293-329; Hirama, M. J. Synth. Org. Chem. Jpn. 1994, 52, 980-991; J. Suffert, R. Brückner, Lettre des Sciences Chimiques, février-avril 1996, 25-29; H. Lhermitte, D. Grierson, Contemp. Org. Synth. 1996, 3, 93-124; J. W. Grissom, G. U. Gunawardena, D, Klingberg, D. Huang, Tetrahedron 1996, 52, 6453-6518.
10. Isolation and purification of neocarzinostatin: J. Shoji, J. Antibiot. 1961, 14, 27-33; N. Ishida, M. Miyazaki, K. Kumagai, M. Rikimaru, J. Antibiot. 1965, 18, 68-76. Gross composition of neocarzinostatin: M. A. Napier, B. Holmquist, D. J. Strydom, I. H. Goldberg, Biochem. Biophys. Res. Comm. 1979, 89, 635-642; Y. Koide, F. Ishi, K. Hasuda, Y. Koyama, K. Edo, S. Katamine, F. Kitame, N. Ishida, J. Antibiot. 1980, 33, 342-346. Biology of neocarzinostatin: Goldberg; I. H. Acc. Chem. Res. 1991, 24, 191-198; Saito, I. Toxicol. Lett. 1993, 67, 3-15. H. Maeda, K. Edo, N. Ishida, Neocarzinostatin, Springer, Tokyo, 1997. Chemistry of neocarzinostatin and analogs thereof: Hirama, M. in Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products, Vol. 2 (G. Lukacs, Ed.), Springer, Berlin, 1993, 293-329; Hirama, M. J. Synth. Org. Chem. Jpn. 1994, 52, 980-991; J. Suffert, R. Brückner, Lettre des Sciences Chimiques, février-avril 1996, 25-29; H. Lhermitte, D. Grierson, Contemp. Org. Synth. 1996, 3, 93-124; J. W. Grissom, G. U. Gunawardena, D, Klingberg, D. Huang, Tetrahedron 1996, 52, 6453-6518.
11. Isolation and purification of neocarzinostatin: J. Shoji, J. Antibiot. 1961, 14, 27-33; N. Ishida, M. Miyazaki, K. Kumagai, M. Rikimaru, J. Antibiot. 1965, 18, 68-76. Gross composition of neocarzinostatin: M. A. Napier, B. Holmquist, D. J. Strydom, I. H. Goldberg, Biochem. Biophys. Res. Comm. 1979, 89, 635-642; Y. Koide, F. Ishi, K. Hasuda, Y. Koyama, K. Edo, S. Katamine, F. Kitame, N. Ishida, J. Antibiot. 1980, 33, 342-346. Biology of neocarzinostatin: Goldberg; I. H. Acc. Chem. Res. 1991, 24, 191-198; Saito, I. Toxicol. Lett. 1993, 67, 3-15. H. Maeda, K. Edo, N. Ishida, Neocarzinostatin, Springer, Tokyo, 1997. Chemistry of neocarzinostatin and analogs thereof: Hirama, M. in Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products, Vol. 2 (G. Lukacs, Ed.), Springer, Berlin, 1993, 293-329; Hirama, M. J. Synth. Org. Chem. Jpn. 1994, 52, 980-991; J. Suffert, R. Brückner, Lettre des Sciences Chimiques, février-avril 1996, 25-29; H. Lhermitte, D. Grierson, Contemp. Org. Synth. 1996, 3, 93-124; J. W. Grissom, G. U. Gunawardena, D, Klingberg, D. Huang, Tetrahedron 1996, 52, 6453-6518.
12. Isolation and purification of neocarzinostatin: J. Shoji, J. Antibiot. 1961, 14, 27-33; N. Ishida, M. Miyazaki, K. Kumagai, M. Rikimaru, J. Antibiot. 1965, 18, 68-76. Gross composition of neocarzinostatin: M. A. Napier, B. Holmquist, D. J. Strydom, I. H. Goldberg, Biochem. Biophys. Res. Comm. 1979, 89, 635-642; Y. Koide, F. Ishi, K. Hasuda, Y. Koyama, K. Edo, S. Katamine, F. Kitame, N. Ishida, J. Antibiot. 1980, 33, 342-346. Biology of neocarzinostatin: Goldberg; I. H. Acc. Chem. Res. 1991, 24, 191-198; Saito, I. Toxicol. Lett. 1993, 67, 3-15. H. Maeda, K. Edo, N. Ishida, Neocarzinostatin, Springer, Tokyo, 1997. Chemistry of neocarzinostatin and analogs thereof: Hirama, M. in Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products, Vol. 2 (G. Lukacs, Ed.), Springer, Berlin, 1993, 293-329; Hirama, M. J. Synth. Org. Chem. Jpn. 1994, 52, 980-991; J. Suffert, R. Brückner, Lettre des Sciences Chimiques, février-avril 1996, 25-29; H. Lhermitte, D. Grierson, Contemp. Org. Synth. 1996, 3, 93-124; J. W. Grissom, G. U. Gunawardena, D, Klingberg, D. Huang, Tetrahedron 1996, 52, 6453-6518.
13. Constitution of chromophore: K. Edo, M. Mizugaki, Y. Koide, H. Seto, K. Furihata, N. Otake, N. Ishida, Tetrahedron Lett. 1985, 26, 331-334. Stereostructure of sugar moiety: K. Edo, Y. Akiyama, K. Saito, M. Mizugaki, Y. Koide, N. Ishida, J. Antibiot. 1986, 39, 1615-1619. Stereostructure of aglycon: A. G. Myers, P. J. Proteau, T. M. Handel, J. Am. Chem. Soc. 1988, 110, 7212-7214. Conformation of neocarzinostatin in solution: T. Tanaka, M. Hirama, K.-i. Fujita, S. Imajo, M. Ishiguro, J. Chem. Soc. Chem. Commun. 1993, 1205-1207. 3-Dimensional structure of neocarzinostatin in the solid state: K. H. Kim, B. M. Kwon, A. G. Myers, D. C. Rees, Science 1993, 262, 1042-1046.
14. Constitution of chromophore: K. Edo, M. Mizugaki, Y. Koide, H. Seto, K. Furihata, N. Otake, N. Ishida, Tetrahedron Lett. 1985, 26, 331-334. Stereostructure of sugar moiety: K. Edo, Y. Akiyama, K. Saito, M. Mizugaki, Y. Koide, N. Ishida, J. Antibiot. 1986, 39, 1615-1619. Stereostructure of aglycon: A. G. Myers, P. J. Proteau, T. M. Handel, J. Am. Chem. Soc. 1988, 110, 7212-7214. Conformation of neocarzinostatin in solution: T. Tanaka, M. Hirama, K.-i. Fujita, S. Imajo, M. Ishiguro, J. Chem. Soc. Chem. Commun. 1993, 1205-1207. 3-Dimensional structure of neocarzinostatin in the solid state: K. H. Kim, B. M. Kwon, A. G. Myers, D. C. Rees, Science 1993, 262, 1042-1046.
15. Constitution of chromophore: K. Edo, M. Mizugaki, Y. Koide, H. Seto, K. Furihata, N. Otake, N. Ishida, Tetrahedron Lett. 1985, 26, 331-334. Stereostructure of sugar moiety: K. Edo, Y. Akiyama, K. Saito, M. Mizugaki, Y. Koide, N. Ishida, J. Antibiot. 1986, 39, 1615-1619. Stereostructure of aglycon: A. G. Myers, P. J. Proteau, T. M. Handel, J. Am. Chem. Soc. 1988, 110, 7212-7214. Conformation of neocarzinostatin in solution: T. Tanaka, M. Hirama, K.-i. Fujita, S. Imajo, M. Ishiguro, J. Chem. Soc. Chem. Commun. 1993, 1205-1207. 3-Dimensional structure of neocarzinostatin in the solid state: K. H. Kim, B. M. Kwon, A. G. Myers, D. C. Rees, Science 1993, 262, 1042-1046.
16. Constitution of chromophore: K. Edo, M. Mizugaki, Y. Koide, H. Seto, K. Furihata, N. Otake, N. Ishida, Tetrahedron Lett. 1985, 26, 331-334. Stereostructure of sugar moiety: K. Edo, Y. Akiyama, K. Saito, M. Mizugaki, Y. Koide, N. Ishida, J. Antibiot. 1986, 39, 1615-1619. Stereostructure of aglycon: A. G. Myers, P. J. Proteau, T. M. Handel, J. Am. Chem. Soc. 1988, 110, 7212-7214. Conformation of neocarzinostatin in solution: T. Tanaka, M. Hirama, K.-i. Fujita, S. Imajo, M. Ishiguro, J. Chem. Soc. Chem. Commun. 1993, 1205-1207. 3-Dimensional structure of neocarzinostatin in the solid state: K. H. Kim, B. M. Kwon, A. G. Myers, D. C. Rees, Science 1993, 262, 1042-1046.
17. Constitution of chromophore: K. Edo, M. Mizugaki, Y. Koide, H. Seto, K. Furihata, N. Otake, N. Ishida, Tetrahedron Lett. 1985, 26, 331-334. Stereostructure of sugar moiety: K. Edo, Y. Akiyama, K. Saito, M. Mizugaki, Y. Koide, N. Ishida, J. Antibiot. 1986, 39, 1615-1619. Stereostructure of aglycon: A. G. Myers, P. J. Proteau, T. M. Handel, J. Am. Chem. Soc. 1988, 110, 7212-7214. Conformation of neocarzinostatin in solution: T. Tanaka, M. Hirama, K.-i. Fujita, S. Imajo, M. Ishiguro, J. Chem. Soc. Chem. Commun. 1993, 1205-1207. 3-Dimensional structure of neocarzinostatin in the solid state: K. H. Kim, B. M. Kwon, A. G. Myers, D. C. Rees, Science 1993, 262, 1042-1046.
18. A sugar-free naphthoyloxy-substituted dienediyne epoxydiol closely related to NCS was recently identified as antibiotic N1999A2 by T. Ando, M. Ishii, T. Kajiura, T. Kameyama, K. Miwa, Y. Sugiura, Tetrahedron Lett. 1998, 39, 6495-6498.
19. Cf. ref. 3 cited in K. Toshima, K. Ohta, K. Yanagawa, T. Kano, M. Nakata, M. Kinoshita, S. Matsumura, J. Am. Chem. Soc. 1995, 117, 10825-10831.
20. A. G. Myers, J. Liang, M. Hammond, P. M. Harrington, Y. Wu, E. Y. Kuo, J. Am. Chem. Soc. 1998, 120, 5319-5320.
21. A. G. Myers, M. Hammond, Y. Wu, J.-N, Xiang, P. M. Harrington, E. Y. Kuo, J. Am. Chem. Soc. 1996, 118, 10006-10007.
22. S. Kawata, Yoshimura, J. Irie, H. Ehara, M. Hirama, Synlett 1997, 250-252; corrigendum ibid. 740.
23. S. Kawata, Yoshimura, J. Irie, H. Ehara, M. Hirama, Synlett 1997, 250-252; corrigendum ibid. 740.
24. T. Takahashi, H. Tanaka, H. Yamada, T. Matsumoto, Y. Sugiura, Angew. Chem. 1997, 109, 1570-1572.
25. Induction by thiolate: a) A. G. Myers, Tetrahedron Lett. 1987, 28, 4493-4496;
26. b) A. G. Myers, P. J. Proteau, J. Am. Chem. Soc. 1989, 111, 1146-1147;
27. c) A. G. Myers, S. B. Cohen, B.-M. Kwon, J. Am. Chem. Soc. 1994, 116, 1670-1682;
28. d) H. Sugiyama, T. Fujiwara, I. Saito, Tetrahedron Lett. 1994, 35, 8825-8828;
29. e) D.-H. Chin, M.-C. Tseng, Tetrahedron Lett. 1997, 38, 2891-2894.
30. Aerobic induction: f) T. Tanaka, K. Fujiwara, M. Hirama, Tetrahedron Lett. 1990, 31, 5947-5950.
31. Induction by base: g) O. D, Hensens, G. L. Helms, D. L. Zink, D.-H. Chin, L. S. Kappen, I. H. Goldberg, J. Am. Chem. Soc. 1993, 115, 11030-11031.
32. h) Induction by light: T. Gomibuchi, M. Hirama, J. Antibiot. 1995, 48, 738-740.-
33. Cf. also the desactivation of protein-bound neocarzinostatin chromophore by thiols: i) H. Sugiyama, K. Yamashita, T. Fujiwara, I. Saito, Tetrahedron 1994, 50, 1311-1325;
34. j) A. G. Myers, S. P. Arvedson, R. W. Lee, J. Am. Chem. Soc. 1996, 118, 4725-4726.
35. The intermediacy of enyneallene 8 postulated in Schemes 2 and 4 is an alternative for the intermediates suggested to form 13 according to ref. 9i. Experimentally, no intermediate has been identified.
36. A. G. Myers, P. M. Harrington, B.-M. Kwon, J. Am. Chem. Soc. 1992, 114, 1086-1087.
37. Recent examples and related reactions include: A. Tarli, K. K. Wang, J. Org. Chem. 1997, 62, 8841-8847; J. Haffner, M. J. Schottelius, D. Feichtinger, P. Chen, J. Am. Chem. Soc. 1998, 120, 376-385; M. H. Nantz, D. K. Moss, J. D. Spence, M. M. Olmstead, Angew. Chem. 1998, 110, 476-478; Angew. Chem. Int. Ed. Engl. 1998, 37, 470-473; P. R. Schreiner, J. Chem. Soc. Chem. Commun. 1998, 483-484; C. S. Shi, K. K. Wang, J. Org. Chem. 1998, 63, 3517-3520; M. Schmittel, J.-P. Steffen, M. A. W. Angel, B. Engels, C. Lennartz, M. Hanrath, Angew. Chem. 1998, 110, 1633-1635; Angew. Chem. Int. Ed. Engl. 1998, 37, 1562-1564; L. Banfi, G. Guanti, Eur. J. Org. Chem. 1998, 1543-1548; K. Miyawaki, T. Kawano, I. Ueda, Tetrahedron Lett. 1998, 39, 6923-6926; P. R. Schreiner, J. Am. Chem. Soc. 1998, 120, 4184-4190; C. J. Cramer, J. Am. Chem. Soc. 1998, 120, 6261-6269; M. Schmittel, J.-P. Steffen, B. Engels, C. Lennartz, M. Hanrath, Angew. Chem. 1998, 110, 2531-2533; Angew. Chem. Int. Ed. Engl. 1998, 37, 2371-2373.
38. Recent examples and related reactions include: A. Tarli, K. K. Wang, J. Org. Chem. 1997, 62, 8841-8847; J. Haffner, M. J. Schottelius, D. Feichtinger, P. Chen, J. Am. Chem. Soc. 1998, 120, 376-385; M. H. Nantz, D. K. Moss, J. D. Spence, M. M. Olmstead, Angew. Chem. 1998, 110, 476-478; Angew. Chem. Int. Ed. Engl. 1998, 37, 470-473; P. R. Schreiner, J. Chem. Soc. Chem. Commun. 1998, 483-484; C. S. Shi, K. K. Wang, J. Org. Chem. 1998, 63, 3517-3520; M. Schmittel, J.-P. Steffen, M. A. W. Angel, B. Engels, C. Lennartz, M. Hanrath, Angew. Chem. 1998, 110, 1633-1635; Angew. Chem. Int. Ed. Engl. 1998, 37, 1562-1564; L. Banfi, G. Guanti, Eur. J. Org. Chem. 1998, 1543-1548; K. Miyawaki, T. Kawano, I. Ueda, Tetrahedron Lett. 1998, 39, 6923-6926; P. R. Schreiner, J. Am. Chem. Soc. 1998, 120, 4184-4190; C. J. Cramer, J. Am. Chem. Soc. 1998, 120, 6261-6269; M. Schmittel, J.-P. Steffen, B. Engels, C. Lennartz, M. Hanrath, Angew. Chem. 1998, 110, 2531-2533; Angew. Chem. Int. Ed. Engl. 1998, 37, 2371-2373.
39. Recent examples and related reactions include: A. Tarli, K. K. Wang, J. Org. Chem. 1997, 62, 8841-8847; J. Haffner, M. J. Schottelius, D. Feichtinger, P. Chen, J. Am. Chem. Soc. 1998, 120, 376-385; M. H. Nantz, D. K. Moss, J. D. Spence, M. M. Olmstead, Angew. Chem. 1998, 110, 476-478; Angew. Chem. Int. Ed. Engl. 1998, 37, 470-473; P. R. Schreiner, J. Chem. Soc. Chem. Commun. 1998, 483-484; C. S. Shi, K. K. Wang, J. Org. Chem. 1998, 63, 3517-3520; M. Schmittel, J.-P. Steffen, M. A. W. Angel, B. Engels, C. Lennartz, M. Hanrath, Angew. Chem. 1998, 110, 1633-1635; Angew. Chem. Int. Ed. Engl. 1998, 37, 1562-1564; L. Banfi, G. Guanti, Eur. J. Org. Chem. 1998, 1543-1548; K. Miyawaki, T. Kawano, I. Ueda, Tetrahedron Lett. 1998, 39, 6923-6926; P. R. Schreiner, J. Am. Chem. Soc. 1998, 120, 4184-4190; C. J. Cramer, J. Am. Chem. Soc. 1998, 120, 6261-6269; M. Schmittel, J.-P. Steffen, B. Engels, C. Lennartz, M. Hanrath, Angew. Chem. 1998, 110, 2531-2533; Angew. Chem. Int. Ed. Engl. 1998, 37, 2371-2373.
40. Recent examples and related reactions include: A. Tarli, K. K. Wang, J. Org. Chem. 1997, 62, 8841-8847; J. Haffner, M. J. Schottelius, D. Feichtinger, P. Chen, J. Am. Chem. Soc. 1998, 120, 376-385; M. H. Nantz, D. K. Moss, J. D. Spence, M. M. Olmstead, Angew. Chem. 1998, 110, 476-478; Angew. Chem. Int. Ed. Engl. 1998, 37, 470-473; P. R. Schreiner, J. Chem. Soc. Chem. Commun. 1998, 483-484; C. S. Shi, K. K. Wang, J. Org. Chem. 1998, 63, 3517-3520; M. Schmittel, J.-P. Steffen, M. A. W. Angel, B. Engels, C. Lennartz, M. Hanrath, Angew. Chem. 1998, 110, 1633-1635; Angew. Chem. Int. Ed. Engl. 1998, 37, 1562-1564; L. Banfi, G. Guanti, Eur. J. Org. Chem. 1998, 1543-1548; K. Miyawaki, T. Kawano, I. Ueda, Tetrahedron Lett. 1998, 39, 6923-6926; P. R. Schreiner, J. Am. Chem. Soc. 1998, 120, 4184-4190; C. J. Cramer, J. Am. Chem. Soc. 1998, 120, 6261-6269; M. Schmittel, J.-P. Steffen, B. Engels, C. Lennartz, M. Hanrath, Angew. Chem. 1998, 110, 2531-2533; Angew. Chem. Int. Ed. Engl. 1998, 37, 2371-2373.
41. Recent examples and related reactions include: A. Tarli, K. K. Wang, J. Org. Chem. 1997, 62, 8841-8847; J. Haffner, M. J. Schottelius, D. Feichtinger, P. Chen, J. Am. Chem. Soc. 1998, 120, 376-385; M. H. Nantz, D. K. Moss, J. D. Spence, M. M. Olmstead, Angew. Chem. 1998, 110, 476-478; Angew. Chem. Int. Ed. Engl. 1998, 37, 470-473; P. R. Schreiner, J. Chem. Soc. Chem. Commun. 1998, 483-484; C. S. Shi, K. K. Wang, J. Org. Chem. 1998, 63, 3517-3520; M. Schmittel, J.-P. Steffen, M. A. W. Angel, B. Engels, C. Lennartz, M. Hanrath, Angew. Chem. 1998, 110, 1633-1635; Angew. Chem. Int. Ed. Engl. 1998, 37, 1562-1564; L. Banfi, G. Guanti, Eur. J. Org. Chem. 1998, 1543-1548; K. Miyawaki, T. Kawano, I. Ueda, Tetrahedron Lett. 1998, 39, 6923-6926; P. R. Schreiner, J. Am. Chem. Soc. 1998, 120, 4184-4190; C. J. Cramer, J. Am. Chem. Soc. 1998, 120, 6261-6269; M. Schmittel, J.-P. Steffen, B. Engels, C. Lennartz, M. Hanrath, Angew. Chem. 1998, 110, 2531-2533; Angew. Chem. Int. Ed. Engl. 1998, 37, 2371-2373.
42. Recent examples and related reactions include: A. Tarli, K. K. Wang, J. Org. Chem. 1997, 62, 8841-8847; J. Haffner, M. J. Schottelius, D. Feichtinger, P. Chen, J. Am. Chem. Soc. 1998, 120, 376-385; M. H. Nantz, D. K. Moss, J. D. Spence, M. M. Olmstead, Angew. Chem. 1998, 110, 476-478; Angew. Chem. Int. Ed. Engl. 1998, 37, 470-473; P. R. Schreiner, J. Chem. Soc. Chem. Commun. 1998, 483-484; C. S. Shi, K. K. Wang, J. Org. Chem. 1998, 63, 3517-3520; M. Schmittel, J.-P. Steffen, M. A. W. Angel, B. Engels, C. Lennartz, M. Hanrath, Angew. Chem. 1998, 110, 1633-1635; Angew. Chem. Int. Ed. Engl. 1998, 37, 1562-1564; L. Banfi, G. Guanti, Eur. J. Org. Chem. 1998, 1543-1548; K. Miyawaki, T. Kawano, I. Ueda, Tetrahedron Lett. 1998, 39, 6923-6926; P. R. Schreiner, J. Am. Chem. Soc. 1998, 120, 4184-4190; C. J. Cramer, J. Am. Chem. Soc. 1998, 120, 6261-6269; M. Schmittel, J.-P. Steffen, B. Engels, C. Lennartz, M. Hanrath, Angew. Chem. 1998, 110, 2531-2533; Angew. Chem. Int. Ed. Engl. 1998, 37, 2371-2373.
43. Recent examples and related reactions include: A. Tarli, K. K. Wang, J. Org. Chem. 1997, 62, 8841-8847; J. Haffner, M. J. Schottelius, D. Feichtinger, P. Chen, J. Am. Chem. Soc. 1998, 120, 376-385; M. H. Nantz, D. K. Moss, J. D. Spence, M. M. Olmstead, Angew. Chem. 1998, 110, 476-478; Angew. Chem. Int. Ed. Engl. 1998, 37, 470-473; P. R. Schreiner, J. Chem. Soc. Chem. Commun. 1998, 483-484; C. S. Shi, K. K. Wang, J. Org. Chem. 1998, 63, 3517-3520; M. Schmittel, J.-P. Steffen, M. A. W. Angel, B. Engels, C. Lennartz, M. Hanrath, Angew. Chem. 1998, 110, 1633-1635; Angew. Chem. Int. Ed. Engl. 1998, 37, 1562-1564; L. Banfi, G. Guanti, Eur. J. Org. Chem. 1998, 1543-1548; K. Miyawaki, T. Kawano, I. Ueda, Tetrahedron Lett. 1998, 39, 6923-6926; P. R. Schreiner, J. Am. Chem. Soc. 1998, 120, 4184-4190; C. J. Cramer, J. Am. Chem. Soc. 1998, 120, 6261-6269; M. Schmittel, J.-P. Steffen, B. Engels, C. Lennartz, M. Hanrath, Angew. Chem. 1998, 110, 2531-2533; Angew. Chem. Int. Ed. Engl. 1998, 37, 2371-2373.
44. Recent examples and related reactions include: A. Tarli, K. K. Wang, J. Org. Chem. 1997, 62, 8841-8847; J. Haffner, M. J. Schottelius, D. Feichtinger, P. Chen, J. Am. Chem. Soc. 1998, 120, 376-385; M. H. Nantz, D. K. Moss, J. D. Spence, M. M. Olmstead, Angew. Chem. 1998, 110, 476-478; Angew. Chem. Int. Ed. Engl. 1998, 37, 470-473; P. R. Schreiner, J. Chem. Soc. Chem. Commun. 1998, 483-484; C. S. Shi, K. K. Wang, J. Org. Chem. 1998, 63, 3517-3520; M. Schmittel, J.-P. Steffen, M. A. W. Angel, B. Engels, C. Lennartz, M. Hanrath, Angew. Chem. 1998, 110, 1633-1635; Angew. Chem. Int. Ed. Engl. 1998, 37, 1562-1564; L. Banfi, G. Guanti, Eur. J. Org. Chem. 1998, 1543-1548; K. Miyawaki, T. Kawano, I. Ueda, Tetrahedron Lett. 1998, 39, 6923-6926; P. R. Schreiner, J. Am. Chem. Soc. 1998, 120, 4184-4190; C. J. Cramer, J. Am. Chem. Soc. 1998, 120, 6261-6269; M. Schmittel, J.-P. Steffen, B. Engels, C. Lennartz, M. Hanrath, Angew. Chem. 1998, 110, 2531-2533; Angew. Chem. Int. Ed. Engl. 1998, 37, 2371-2373.
45. Recent examples and related reactions include: A. Tarli, K. K. Wang, J. Org. Chem. 1997, 62, 8841-8847; J. Haffner, M. J. Schottelius, D. Feichtinger, P. Chen, J. Am. Chem. Soc. 1998, 120, 376-385; M. H. Nantz, D. K. Moss, J. D. Spence, M. M. Olmstead, Angew. Chem. 1998, 110, 476-478; Angew. Chem. Int. Ed. Engl. 1998, 37, 470-473; P. R. Schreiner, J. Chem. Soc. Chem. Commun. 1998, 483-484; C. S. Shi, K. K. Wang, J. Org. Chem. 1998, 63, 3517-3520; M. Schmittel, J.-P. Steffen, M. A. W. Angel, B. Engels, C. Lennartz, M. Hanrath, Angew. Chem. 1998, 110, 1633-1635; Angew. Chem. Int. Ed. Engl. 1998, 37, 1562-1564; L. Banfi, G. Guanti, Eur. J. Org. Chem. 1998, 1543-1548; K. Miyawaki, T. Kawano, I. Ueda, Tetrahedron Lett. 1998, 39, 6923-6926; P. R. Schreiner, J. Am. Chem. Soc. 1998, 120, 4184-4190; C. J. Cramer, J. Am. Chem. Soc. 1998, 120, 6261-6269; M. Schmittel, J.-P. Steffen, B. Engels, C. Lennartz, M. Hanrath, Angew. Chem. 1998, 110, 2531-2533; Angew. Chem. Int. Ed. Engl. 1998, 37, 2371-2373.
46. Recent examples and related reactions include: A. Tarli, K. K. Wang, J. Org. Chem. 1997, 62, 8841-8847; J. Haffner, M. J. Schottelius, D. Feichtinger, P. Chen, J. Am. Chem. Soc. 1998, 120, 376-385; M. H. Nantz, D. K. Moss, J. D. Spence, M. M. Olmstead, Angew. Chem. 1998, 110, 476-478; Angew. Chem. Int. Ed. Engl. 1998, 37, 470-473; P. R. Schreiner, J. Chem. Soc. Chem. Commun. 1998, 483-484; C. S. Shi, K. K. Wang, J. Org. Chem. 1998, 63, 3517-3520; M. Schmittel, J.-P. Steffen, M. A. W. Angel, B. Engels, C. Lennartz, M. Hanrath, Angew. Chem. 1998, 110, 1633-1635; Angew. Chem. Int. Ed. Engl. 1998, 37, 1562-1564; L. Banfi, G. Guanti, Eur. J. Org. Chem. 1998, 1543-1548; K. Miyawaki, T. Kawano, I. Ueda, Tetrahedron Lett. 1998, 39, 6923-6926; P. R. Schreiner, J. Am. Chem. Soc. 1998, 120, 4184-4190; C. J. Cramer, J. Am. Chem. Soc. 1998, 120, 6261-6269; M. Schmittel, J.-P. Steffen, B. Engels, C. Lennartz, M. Hanrath, Angew. Chem. 1998, 110, 2531-2533; Angew. Chem. Int. Ed. Engl. 1998, 37, 2371-2373.
47. Recent examples and related reactions include: A. Tarli, K. K. Wang, J. Org. Chem. 1997, 62, 8841-8847; J. Haffner, M. J. Schottelius, D. Feichtinger, P. Chen, J. Am. Chem. Soc. 1998, 120, 376-385; M. H. Nantz, D. K. Moss, J. D. Spence, M. M. Olmstead, Angew. Chem. 1998, 110, 476-478; Angew. Chem. Int. Ed. Engl. 1998, 37, 470-473; P. R. Schreiner, J. Chem. Soc. Chem. Commun. 1998, 483-484; C. S. Shi, K. K. Wang, J. Org. Chem. 1998, 63, 3517-3520; M. Schmittel, J.-P. Steffen, M. A. W. Angel, B. Engels, C. Lennartz, M. Hanrath, Angew. Chem. 1998, 110, 1633-1635; Angew. Chem. Int. Ed. Engl. 1998, 37, 1562-1564; L. Banfi, G. Guanti, Eur. J. Org. Chem. 1998, 1543-1548; K. Miyawaki, T. Kawano, I. Ueda, Tetrahedron Lett. 1998, 39, 6923-6926; P. R. Schreiner, J. Am. Chem. Soc. 1998, 120, 4184-4190; C. J. Cramer, J. Am. Chem. Soc. 1998, 120, 6261-6269; M. Schmittel, J.-P. Steffen, B. Engels, C. Lennartz, M. Hanrath, Angew. Chem. 1998, 110, 2531-2533; Angew. Chem. Int. Ed. Engl. 1998, 37, 2371-2373.
48. Recent examples and related reactions include: A. Tarli, K. K. Wang, J. Org. Chem. 1997, 62, 8841-8847; J. Haffner, M. J. Schottelius, D. Feichtinger, P. Chen, J. Am. Chem. Soc. 1998, 120, 376-385; M. H. Nantz, D. K. Moss, J. D. Spence, M. M. Olmstead, Angew. Chem. 1998, 110, 476-478; Angew. Chem. Int. Ed. Engl. 1998, 37, 470-473; P. R. Schreiner, J. Chem. Soc. Chem. Commun. 1998, 483-484; C. S. Shi, K. K. Wang, J. Org. Chem. 1998, 63, 3517-3520; M. Schmittel, J.-P. Steffen, M. A. W. Angel, B. Engels, C. Lennartz, M. Hanrath, Angew. Chem. 1998, 110, 1633-1635; Angew. Chem. Int. Ed. Engl. 1998, 37, 1562-1564; L. Banfi, G. Guanti, Eur. J. Org. Chem. 1998, 1543-1548; K. Miyawaki, T. Kawano, I. Ueda, Tetrahedron Lett. 1998, 39, 6923-6926; P. R. Schreiner, J. Am. Chem. Soc. 1998, 120, 4184-4190; C. J. Cramer, J. Am. Chem. Soc. 1998, 120, 6261-6269; M. Schmittel, J.-P. Steffen, B. Engels, C. Lennartz, M. Hanrath, Angew. Chem. 1998, 110, 2531-2533; Angew. Chem. Int. Ed. Engl. 1998, 37, 2371-2373.
49. Recent examples and related reactions include: A. Tarli, K. K. Wang, J. Org. Chem. 1997, 62, 8841-8847; J. Haffner, M. J. Schottelius, D. Feichtinger, P. Chen, J. Am. Chem. Soc. 1998, 120, 376-385; M. H. Nantz, D. K. Moss, J. D. Spence, M. M. Olmstead, Angew. Chem. 1998, 110, 476-478; Angew. Chem. Int. Ed. Engl. 1998, 37, 470-473; P. R. Schreiner, J. Chem. Soc. Chem. Commun. 1998, 483-484; C. S. Shi, K. K. Wang, J. Org. Chem. 1998, 63, 3517-3520; M. Schmittel, J.-P. Steffen, M. A. W. Angel, B. Engels, C. Lennartz, M. Hanrath, Angew. Chem. 1998, 110, 1633-1635; Angew. Chem. Int. Ed. Engl. 1998, 37, 1562-1564; L. Banfi, G. Guanti, Eur. J. Org. Chem. 1998, 1543-1548; K. Miyawaki, T. Kawano, I. Ueda, Tetrahedron Lett. 1998, 39, 6923-6926; P. R. Schreiner, J. Am. Chem. Soc. 1998, 120, 4184-4190; C. J. Cramer, J. Am. Chem. Soc. 1998, 120, 6261-6269; M. Schmittel, J.-P. Steffen, B. Engels, C. Lennartz, M. Hanrath, Angew. Chem. 1998, 110, 2531-2533; Angew. Chem. Int. Ed. Engl. 1998, 37, 2371-2373.
50. Recent examples and related reactions include: A. Tarli, K. K. Wang, J. Org. Chem. 1997, 62, 8841-8847; J. Haffner, M. J. Schottelius, D. Feichtinger, P. Chen, J. Am. Chem. Soc. 1998, 120, 376-385; M. H. Nantz, D. K. Moss, J. D. Spence, M. M. Olmstead, Angew. Chem. 1998, 110, 476-478; Angew. Chem. Int. Ed. Engl. 1998, 37, 470-473; P. R. Schreiner, J. Chem. Soc. Chem. Commun. 1998, 483-484; C. S. Shi, K. K. Wang, J. Org. Chem. 1998, 63, 3517-3520; M. Schmittel, J.-P. Steffen, M. A. W. Angel, B. Engels, C. Lennartz, M. Hanrath, Angew. Chem. 1998, 110, 1633-1635; Angew. Chem. Int. Ed. Engl. 1998, 37, 1562-1564; L. Banfi, G. Guanti, Eur. J. Org. Chem. 1998, 1543-1548; K. Miyawaki, T. Kawano, I. Ueda, Tetrahedron Lett. 1998, 39, 6923-6926; P. R. Schreiner, J. Am. Chem. Soc. 1998, 120, 4184-4190; C. J. Cramer, J. Am. Chem. Soc. 1998, 120, 6261-6269; M. Schmittel, J.-P. Steffen, B. Engels, C. Lennartz, M. Hanrath, Angew. Chem. 1998, 110, 2531-2533; Angew. Chem. Int. Ed. Engl. 1998, 37, 2371-2373.
51. First examples: R. Nagata, H. Yamanaka, E. Okazaki, I. Saito, Tetrahedron Lett. 1989, 30, 4995-4998; A. G. Myers, E. Y. Kuo, N. S. Finney, J. Am. Chem. Soc. 1989, 111, 8057-8059. Next reports: A. G. Myers, P. S. Dragovich, J. Am. Chem. Soc. 1989, 111, 9130-9132; R. Nagata, H. Yamanaka, E. Murahashi, I. Saito, Tetrahedron Lett. 1990, 31, 2907-2910.
52. First examples: R. Nagata, H. Yamanaka, E. Okazaki, I. Saito, Tetrahedron Lett. 1989, 30, 4995-4998; A. G. Myers, E. Y. Kuo, N. S. Finney, J. Am. Chem. Soc. 1989, 111, 8057-8059. Next reports: A. G. Myers, P. S. Dragovich, J. Am. Chem. Soc. 1989, 111, 9130-9132; R. Nagata, H. Yamanaka, E. Murahashi, I. Saito, Tetrahedron Lett. 1990, 31, 2907-2910.
53. First examples: R. Nagata, H. Yamanaka, E. Okazaki, I. Saito, Tetrahedron Lett. 1989, 30, 4995-4998; A. G. Myers, E. Y. Kuo, N. S. Finney, J. Am. Chem. Soc. 1989, 111, 8057-8059. Next reports: A. G. Myers, P. S. Dragovich, J. Am. Chem. Soc. 1989, 111, 9130-9132; R. Nagata, H. Yamanaka, E. Murahashi, I. Saito, Tetrahedron Lett. 1990, 31, 2907-2910.
54. First examples: R. Nagata, H. Yamanaka, E. Okazaki, I. Saito, Tetrahedron Lett. 1989, 30, 4995-4998; A. G. Myers, E. Y. Kuo, N. S. Finney, J. Am. Chem. Soc. 1989, 111, 8057-8059. Next reports: A. G. Myers, P. S. Dragovich, J. Am. Chem. Soc. 1989, 111, 9130-9132; R. Nagata, H. Yamanaka, E. Murahashi, I. Saito, Tetrahedron Lett. 1990, 31, 2907-2910.
55. Matrix isolation and calculations of a toluene biradical: W. Sander, H. Wandel, G. Bucher, J. Gräfenstein, E. Kraka, D. Cremer, J. Am. Chem. Soc, 1998, 120, 8480-8485.
56. N. Krause, Hohmann, Synlett 1996, 89-91, corrigendum 590; K. K. Wang, Z. Wang, A. Tarli, P. Garrett, J. Am. Chem. Soc. 1996, 118, 10783-10791; R. F. Cunico, S. K. Nair, Tetrahedron Lett. 1997, 38, 25-28; I. Suzuki, Y. Naoe, M. Bando, H. Nemoto, M. Shibuya, Tetrahedron Lett. 1998, 39, 2361-2364 and references cited therein.
57. N. Krause, Hohmann, Synlett 1996, 89-91, corrigendum 590; K. K. Wang, Z. Wang, A. Tarli, P. Garrett, J. Am. Chem. Soc. 1996, 118, 10783-10791; R. F. Cunico, S. K. Nair, Tetrahedron Lett. 1997, 38, 25-28; I. Suzuki, Y. Naoe, M. Bando, H. Nemoto, M. Shibuya, Tetrahedron Lett. 1998, 39, 2361-2364 and references cited therein.
58. N. Krause, Hohmann, Synlett 1996, 89-91, corrigendum 590; K. K. Wang, Z. Wang, A. Tarli, P. Garrett, J. Am. Chem. Soc. 1996, 118, 10783-10791; R. F. Cunico, S. K. Nair, Tetrahedron Lett. 1997, 38, 25-28; I. Suzuki, Y. Naoe, M. Bando, H. Nemoto, M. Shibuya, Tetrahedron Lett. 1998, 39, 2361-2364 and references cited therein.
59. N. Krause, Hohmann, Synlett 1996, 89-91, corrigendum 590; K. K. Wang, Z. Wang, A. Tarli, P. Garrett, J. Am. Chem. Soc. 1996, 118, 10783-10791; R. F. Cunico, S. K. Nair, Tetrahedron Lett. 1997, 38, 25-28; I. Suzuki, Y. Naoe, M. Bando, H. Nemoto, M. Shibuya, Tetrahedron Lett. 1998, 39, 2361-2364 and references cited therein.
60. S. W. Scheuplein, R. Machinek, J. Suffert, R. Brückner, Tetrahedron Lett. 1993, 34, 6549-6552.
61. First examples: M. Schmittel, M. Strittmatter, S. Kiau, Tetrahedron Lett. 1995, 36, 4975-4978.
62. Theoretical treatment of a Schmittel cyclization: B. Engels, C. Lennartz, M. Hanrath, M. Schmittel, M. Strittmatter, Angew. Chem. 1998, 110, 2067-2070; Angew. Chem. Int. Ed. Engl. 1998, 37, 1960-1963.
63. Theoretical treatment of a Schmittel cyclization: B. Engels, C. Lennartz, M. Hanrath, M. Schmittel, M. Strittmatter, Angew. Chem. 1998, 110, 2067-2070; Angew. Chem. Int. Ed. Engl. 1998, 37, 1960-1963.
64. The only bis(enol triflates) before ours of which we are aware were derived from 1,3-cyclohexanediones (A. García Martínez, R. Martínez Alvarez, M. Madueño Casado, L. R. Subramanian, M. Hanack, Tetrahedron 1987, 43, 275-279) but not coupled with nucleophiles.
65. Identical approaches both to Z-and E-configured dienediynes derived from Z-and E-4 and containing two identical alkyne arms (K. Nakatani, K. Arai, K. Yamada, S. Terashima, Tetrahedron Lett. 1991, 32, 3405-3406) or different ones (K. Nakatani, K. Arai, K. Yamada, S. Terashima, Tetrahedron 1992, 48, 3045-3060; cf. also K. Nakatani, K. Arai, S. Terashima, J. Chem. Soc., Chem. Commun. 1992, 289-291) were published after ours (ref. 21/24 and 22, respectively). Stereospecific monocouplings between monotriflates Z-or E-36 and 3,4-epoxy-1-alkynes were reported by P. Bertus, P. Pale, Tetrahedron Lett. 1997, 38, 8193-8196; corrigendum Tetrahedron Lett. 1998, 39, 1843. (Recetnly, successive Pd-catalyzed couplings between Z-1-chloro-3-iodo-1,3-diene and two terminal alkynes were shown to afford acyclic Z-configured dienediyne models of NCS by M. Bujard, F. Ferri, M. Alami, Tetrahedron Lett. 1998, 39, 4243-4246.
66. Identical approaches both to Z-and E-configured dienediynes derived from Z-and E-4 and containing two identical alkyne arms (K. Nakatani, K. Arai, K. Yamada, S. Terashima, Tetrahedron Lett. 1991, 32, 3405-3406) or different ones (K. Nakatani, K. Arai, K. Yamada, S. Terashima, Tetrahedron 1992, 48, 3045-3060; cf. also K. Nakatani, K. Arai, S. Terashima, J. Chem. Soc., Chem. Commun. 1992, 289-291) were published after ours (ref. 21/24 and 22, respectively). Stereospecific monocouplings between monotriflates Z-or E-36 and 3,4-epoxy-1-alkynes were reported by P. Bertus, P. Pale, Tetrahedron Lett. 1997, 38, 8193-8196; corrigendum Tetrahedron Lett. 1998, 39, 1843. (Recetnly, successive Pd-catalyzed couplings between Z-1-chloro-3-iodo-1,3-diene and two terminal alkynes were shown to afford acyclic Z-configured dienediyne models of NCS by M. Bujard, F. Ferri, M. Alami, Tetrahedron Lett. 1998, 39, 4243-4246.
67. Identical approaches both to Z-and E-configured dienediynes derived from Z-and E-4 and containing two identical alkyne arms (K. Nakatani, K. Arai, K. Yamada, S. Terashima, Tetrahedron Lett. 1991, 32, 3405-3406) or different ones (K. Nakatani, K. Arai, K. Yamada, S. Terashima, Tetrahedron 1992, 48, 3045-3060; cf. also K. Nakatani, K. Arai, S. Terashima, J. Chem. Soc., Chem. Commun. 1992, 289-291) were published after ours (ref. 21/24 and 22, respectively). Stereospecific monocouplings between monotriflates Z-or E-36 and 3,4-epoxy-1-alkynes were reported by P. Bertus, P. Pale, Tetrahedron Lett. 1997, 38, 8193-8196; corrigendum Tetrahedron Lett. 1998, 39, 1843. (Recetnly, successive Pd-catalyzed couplings between Z-1-chloro-3-iodo-1,3-diene and two terminal alkynes were shown to afford acyclic Z-configured dienediyne models of NCS by M. Bujard, F. Ferri, M. Alami, Tetrahedron Lett. 1998, 39, 4243-4246.
68. Identical approaches both to Z-and E-configured dienediynes derived from Z-and E-4 and containing two identical alkyne arms (K. Nakatani, K. Arai, K. Yamada, S. Terashima, Tetrahedron Lett. 1991, 32, 3405-3406) or different ones (K. Nakatani, K. Arai, K. Yamada, S. Terashima, Tetrahedron 1992, 48, 3045-3060; cf. also K. Nakatani, K. Arai, S. Terashima, J. Chem. Soc., Chem. Commun. 1992, 289-291) were published after ours (ref. 21/24 and 22, respectively). Stereospecific monocouplings between monotriflates Z-or E-36 and 3,4-epoxy-1-alkynes were reported by P. Bertus, P. Pale, Tetrahedron Lett. 1997, 38, 8193-8196; corrigendum Tetrahedron Lett. 1998, 39, 1843. (Recetnly, successive Pd-catalyzed couplings between Z-1-chloro-3-iodo-1,3-diene and two terminal alkynes were shown to afford acyclic Z-configured dienediyne models of NCS by M. Bujard, F. Ferri, M. Alami, Tetrahedron Lett. 1998, 39, 4243-4246.
69. Identical approaches both to Z-and E-configured dienediynes derived from Z-and E-4 and containing two identical alkyne arms (K. Nakatani, K. Arai, K. Yamada, S. Terashima, Tetrahedron Lett. 1991, 32, 3405-3406) or different ones (K. Nakatani, K. Arai, K. Yamada, S. Terashima, Tetrahedron 1992, 48, 3045-3060; cf. also K. Nakatani, K. Arai, S. Terashima, J. Chem. Soc., Chem. Commun. 1992, 289-291) were published after ours (ref. 21/24 and 22, respectively). Stereospecific monocouplings between monotriflates Z-or E-36 and 3,4-epoxy-1-alkynes were reported by P. Bertus, P. Pale, Tetrahedron Lett. 1997, 38, 8193-8196; corrigendum Tetrahedron Lett. 1998, 39, 1843. (Recetnly, successive Pd-catalyzed couplings between Z-1-chloro-3-iodo-1,3-diene and two terminal alkynes were shown to afford acyclic Z-configured dienediyne models of NCS by M. Bujard, F. Ferri, M. Alami, Tetrahedron Lett. 1998, 39, 4243-4246.
70. Identical approaches both to Z-and E-configured dienediynes derived from Z-and E-4 and containing two identical alkyne arms (K. Nakatani, K. Arai, K. Yamada, S. Terashima, Tetrahedron Lett. 1991, 32, 3405-3406) or different ones (K. Nakatani, K. Arai, K. Yamada, S. Terashima, Tetrahedron 1992, 48, 3045-3060; cf. also K. Nakatani, K. Arai, S. Terashima, J. Chem. Soc., Chem. Commun. 1992, 289-291) were published after ours (ref. 21/24 and 22, respectively). Stereospecific monocouplings between monotriflates Z-or E-36 and 3,4-epoxy-1-alkynes were reported by P. Bertus, P. Pale, Tetrahedron Lett. 1997, 38, 8193-8196; corrigendum Tetrahedron Lett. 1998, 39, 1843. (Recetnly, successive Pd-catalyzed couplings between Z-1-chloro-3-iodo-1,3-diene and two terminal alkynes were shown to afford acyclic Z-configured dienediyne models of NCS by M. Bujard, F. Ferri, M. Alami, Tetrahedron Lett. 1998, 39, 4243-4246.
71. R. Brückner, S. W. Scheuplein, J. Suffert, Tetrahedron Lett. 1991, 32, 1449-1452.
72. S. W. Scheuplein, K. Harms, R. Brückner, J. Suffert, Chem. Ber. 1992, 125, 271-278.
73. M. Moniatte, M. Eckhardt, K. Brickmann, R. Brückner, J. Suffert, Tetrahedron Lett. 1994, 35, 1965-1968.
74. J. Suffert, R. Brückner, Tetrahedron Lett. 1991, 32, 1453-1456.
75. K. Brickmann, F. Hambloch, J. Suffert, R. Brückner, Liebigs Ann. 1996, 457-471.
76. Method: P. J. Stang, W. Treptow, Synthesis 1980, 283-284; cf. also M. E. Wright, S. R. Pulley, J. Org. Chem. 1989, 54, 2886-2889.
77. Method: P. J. Stang, W. Treptow, Synthesis 1980, 283-284; cf. also M. E. Wright, S. R. Pulley, J. Org. Chem. 1989, 54, 2886-2889.
78. J. Suffert, A. Eggers, S. Scheuplein, R. Brückner, Tetrahedron Lett. 1993, 34, 4177-4180.
79. a) C. P. Casey, D. F. Marten, Tetrahedron Lett. 1974, 925-928.
80. b) F.-W. Sum, L. Weiler, Can. J. Chem. 1979, 57, 1431-1441.
81. c) M. Alderdice, C. Spino, L. Weiler, Tetrahedron Lett. 1984, 25, 1643-1646.-
82. d) M. G. Saulnier, J. F. Kadow, M. M. Tun, D. R, Langley, D. M. Vyas, J. Am. Chem. Soc. 1989, 111, 8320-8321.
83. d) R. M. Keenan, J. Weinstock, J. A. Finkelstein, R. G. Franz, D. E. Gaitanopoulos, G. R. Girard, D. T. Hill, T. M. Morgan, J. M. Samanen, J. Hempel, D. S. Eggelsen, N. Aiyar, E. Griffin, E. H. Ohlstein, E. J. Stack, E. F. Weidley, R. Edwards, J. Med. Chem. 1992, 35, 3858-3872.
84. Ref. 28 b-d; according to ref. 28d sodium β-ketoester enolates are E-rather than Z-configured. in DMF vs. THF
85. Method: J. E. McMurry, W. J. Scott, Tetrahedron Lett. 1983, 24, 979-982.
86. S. W. Scheuplein, Dissertation, Universität Würzburg, 1994;
87. S. W. Scheuplein, R. Brückner, unpublished.
88. Method: S. Cacchi, E. Morera, G. Ortar, Synthesis 1986, 320-322; cf. also K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 1975, 4467-4470.
89. Method: S. Cacchi, E. Morera, G. Ortar, Synthesis 1986, 320-322; cf. also K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 1975, 4467-4470.
90. J. Suffert, R. Brückner, Synlett 1994, 51-53.
91. J. Suffert, E. Abraham, S. Raeppel, R. Brückner, Liebigs Ann. 1996, 447-456.
92. Method: W. J. Scott, J. K. Stille, J. Am. Chem. Soc. 1986, 108, 3033-3040.
93. E. Abraham, Ph. D. Thesis, Strasbourg, 1998.
94. M. Eckhardt, R. Brückner, J. Suffert, Tetrahedron Lett. 1995, 36, 5167-5170.
95. M. Eckhardt, R. Brückner, Liebigs Ann. 1996, 473-488.
96. Method: P. Cintas, Synthesis 1992, 248-257.
97. K. Fujiwara, A. Kurisaki, M. Hirama, Tetrahedron Lett. 1990, 31, 4329-4332.
98. F. Ferri, R. Brückner, R. Herges, New J. Chem. 1998, 22, 531-545; corrigendum 649.
99. Preparation: J. E. McMurry, J. G. Rico, Tetrahedron Lett. 1989, 30, 1169-1172. Characterization: B. Bogdanovic, A. Bolte, J. Organomet. Chem. 1995, 502, 109-121; C. Villiers, M. Ephritikhine, Angew. Chem. 1997, 109, 2477-2479; Angew. Chem. Int. Ed. Engl. 1997, 36, 2380-2382.
100. Preparation: J. E. McMurry, J. G. Rico, Tetrahedron Lett. 1989, 30, 1169-1172. Characterization: B. Bogdanovic, A. Bolte, J. Organomet. Chem. 1995, 502, 109-121; C. Villiers, M. Ephritikhine, Angew. Chem. 1997, 109, 2477-2479; Angew. Chem. Int. Ed. Engl. 1997, 36, 2380-2382.
101. Preparation: J. E. McMurry, J. G. Rico, Tetrahedron Lett. 1989, 30, 1169-1172. Characterization: B. Bogdanovic, A. Bolte, J. Organomet. Chem. 1995, 502, 109-121; C. Villiers, M. Ephritikhine, Angew. Chem. 1997, 109, 2477-2479; Angew. Chem. Int. Ed. Engl. 1997, 36, 2380-2382.
102. Preparation: J. E. McMurry, J. G. Rico, Tetrahedron Lett. 1989, 30, 1169-1172. Characterization: B. Bogdanovic, A. Bolte, J. Organomet. Chem. 1995, 502, 109-121; C. Villiers, M. Ephritikhine, Angew. Chem. 1997, 109, 2477-2479; Angew. Chem. Int. Ed. Engl. 1997, 36, 2380-2382.
103. M. Hirama, K. Fujiwara, K. Shigematu, Y. Fukazawa, J. Am. Chem. Soc. 1989, 111, 4120-4122; ref. 40; P. A. Wender, M. J. Tebbe, Tetrahedron Lett. 1991, 32, 4863-4866 and Tetrahedron 1994, 50, 1419-1434; T. Doi, T. Takahashi, J. Org. Chem. 1991, 56, 3465-3467; M. Hirama, T. Gomibuchi, K. Fujiwara, Y. Sugiura, M. Uesugi, J. Am. Chem. Soc. 1991, 113, 9851-9853; M. Hirama, M. Tokuda, K. Fujiwara, Synlett 1991, 651-653; M. Tokuda, K. Fujiwara, T. Gomibuchi, M. Hirama, M. Uesugi, Y. Sugiura, Tetrahedron Lett. 1993, 34, 669-672; Y. Matsumoto, Y. Kuwatani, I. Ueda, Tetrahedron Lett. 1995, 36, 3197-3200; R. F. Cunico, S. K. Nair, Tetrahedron Lett. 1997, 38, 25-28; S. Caddick, S. Khan, N. J. Smith, D. M. Barr, V. M. Delisser, Tetrahedron Lett. 1997, 38, 5035-5036.
104. M. Hirama, K. Fujiwara, K. Shigematu, Y. Fukazawa, J. Am. Chem. Soc. 1989, 111, 4120-4122; ref. 40; P. A. Wender, M. J. Tebbe, Tetrahedron Lett. 1991, 32, 4863-4866 and Tetrahedron 1994, 50, 1419-1434; T. Doi, T. Takahashi, J. Org. Chem. 1991, 56, 3465-3467; M. Hirama, T. Gomibuchi, K. Fujiwara, Y. Sugiura, M. Uesugi, J. Am. Chem. Soc. 1991, 113, 9851-9853; M. Hirama, M. Tokuda, K. Fujiwara, Synlett 1991, 651-653; M. Tokuda, K. Fujiwara, T. Gomibuchi, M. Hirama, M. Uesugi, Y. Sugiura, Tetrahedron Lett. 1993, 34, 669-672; Y. Matsumoto, Y. Kuwatani, I. Ueda, Tetrahedron Lett. 1995, 36, 3197-3200; R. F. Cunico, S. K. Nair, Tetrahedron Lett. 1997, 38, 25-28; S. Caddick, S. Khan, N. J. Smith, D. M. Barr, V. M. Delisser, Tetrahedron Lett. 1997, 38, 5035-5036.
105. M. Hirama, K. Fujiwara, K. Shigematu, Y. Fukazawa, J. Am. Chem. Soc. 1989, 111, 4120-4122; ref. 40; P. A. Wender, M. J. Tebbe, Tetrahedron Lett. 1991, 32, 4863-4866 and Tetrahedron 1994, 50, 1419-1434; T. Doi, T. Takahashi, J. Org. Chem. 1991, 56, 3465-3467; M. Hirama, T. Gomibuchi, K. Fujiwara, Y. Sugiura, M. Uesugi, J. Am. Chem. Soc. 1991, 113, 9851-9853; M. Hirama, M. Tokuda, K. Fujiwara, Synlett 1991, 651-653; M. Tokuda, K. Fujiwara, T. Gomibuchi, M. Hirama, M. Uesugi, Y. Sugiura, Tetrahedron Lett. 1993, 34, 669-672; Y. Matsumoto, Y. Kuwatani, I. Ueda, Tetrahedron Lett. 1995, 36, 3197-3200; R. F. Cunico, S. K. Nair, Tetrahedron Lett. 1997, 38, 25-28; S. Caddick, S. Khan, N. J. Smith, D. M. Barr, V. M. Delisser, Tetrahedron Lett. 1997, 38, 5035-5036.
106. M. Hirama, K. Fujiwara, K. Shigematu, Y. Fukazawa, J. Am. Chem. Soc. 1989, 111, 4120-4122; ref. 40; P. A. Wender, M. J. Tebbe, Tetrahedron Lett. 1991, 32, 4863-4866 and Tetrahedron 1994, 50, 1419-1434; T. Doi, T. Takahashi, J. Org. Chem. 1991, 56, 3465-3467; M. Hirama, T. Gomibuchi, K. Fujiwara, Y. Sugiura, M. Uesugi, J. Am. Chem. Soc. 1991, 113, 9851-9853; M. Hirama, M. Tokuda, K. Fujiwara, Synlett 1991, 651-653; M. Tokuda, K. Fujiwara, T. Gomibuchi, M. Hirama, M. Uesugi, Y. Sugiura, Tetrahedron Lett. 1993, 34, 669-672; Y. Matsumoto, Y. Kuwatani, I. Ueda, Tetrahedron Lett. 1995, 36, 3197-3200; R. F. Cunico, S. K. Nair, Tetrahedron Lett. 1997, 38, 25-28; S. Caddick, S. Khan, N. J. Smith, D. M. Barr, V. M. Delisser, Tetrahedron Lett. 1997, 38, 5035-5036.
107. M. Hirama, K. Fujiwara, K. Shigematu, Y. Fukazawa, J. Am. Chem. Soc. 1989, 111, 4120-4122; ref. 40; P. A. Wender, M. J. Tebbe, Tetrahedron Lett. 1991, 32, 4863-4866 and Tetrahedron 1994, 50, 1419-1434; T. Doi, T. Takahashi, J. Org. Chem. 1991, 56, 3465-3467; M. Hirama, T. Gomibuchi, K. Fujiwara, Y. Sugiura, M. Uesugi, J. Am. Chem. Soc. 1991, 113, 9851-9853; M. Hirama, M. Tokuda, K. Fujiwara, Synlett 1991, 651-653; M. Tokuda, K. Fujiwara, T. Gomibuchi, M. Hirama, M. Uesugi, Y. Sugiura, Tetrahedron Lett. 1993, 34, 669-672; Y. Matsumoto, Y. Kuwatani, I. Ueda, Tetrahedron Lett. 1995, 36, 3197-3200; R. F. Cunico, S. K. Nair, Tetrahedron Lett. 1997, 38, 25-28; S. Caddick, S. Khan, N. J. Smith, D. M. Barr, V. M. Delisser, Tetrahedron Lett. 1997, 38, 5035-5036.
108. M. Hirama, K. Fujiwara, K. Shigematu, Y. Fukazawa, J. Am. Chem. Soc. 1989, 111, 4120-4122; ref. 40; P. A. Wender, M. J. Tebbe, Tetrahedron Lett. 1991, 32, 4863-4866 and Tetrahedron 1994, 50, 1419-1434; T. Doi, T. Takahashi, J. Org. Chem. 1991, 56, 3465-3467; M. Hirama, T. Gomibuchi, K. Fujiwara, Y. Sugiura, M. Uesugi, J. Am. Chem. Soc. 1991, 113, 9851-9853; M. Hirama, M. Tokuda, K. Fujiwara, Synlett 1991, 651-653; M. Tokuda, K. Fujiwara, T. Gomibuchi, M. Hirama, M. Uesugi, Y. Sugiura, Tetrahedron Lett. 1993, 34, 669-672; Y. Matsumoto, Y. Kuwatani, I. Ueda, Tetrahedron Lett. 1995, 36, 3197-3200; R. F. Cunico, S. K. Nair, Tetrahedron Lett. 1997, 38, 25-28; S. Caddick, S. Khan, N. J. Smith, D. M. Barr, V. M. Delisser, Tetrahedron Lett. 1997, 38, 5035-5036.
109. M. Hirama, K. Fujiwara, K. Shigematu, Y. Fukazawa, J. Am. Chem. Soc. 1989, 111, 4120-4122; ref. 40; P. A. Wender, M. J. Tebbe, Tetrahedron Lett. 1991, 32, 4863-4866 and Tetrahedron 1994, 50, 1419-1434; T. Doi, T. Takahashi, J. Org. Chem. 1991, 56, 3465-3467; M. Hirama, T. Gomibuchi, K. Fujiwara, Y. Sugiura, M. Uesugi, J. Am. Chem. Soc. 1991, 113, 9851-9853; M. Hirama, M. Tokuda, K. Fujiwara, Synlett 1991, 651-653; M. Tokuda, K. Fujiwara, T. Gomibuchi, M. Hirama, M. Uesugi, Y. Sugiura, Tetrahedron Lett. 1993, 34, 669-672; Y. Matsumoto, Y. Kuwatani, I. Ueda, Tetrahedron Lett. 1995, 36, 3197-3200; R. F. Cunico, S. K. Nair, Tetrahedron Lett. 1997, 38, 25-28; S. Caddick, S. Khan, N. J. Smith, D. M. Barr, V. M. Delisser, Tetrahedron Lett. 1997, 38, 5035-5036.
110. M. Hirama, K. Fujiwara, K. Shigematu, Y. Fukazawa, J. Am. Chem. Soc. 1989, 111, 4120-4122; ref. 40; P. A. Wender, M. J. Tebbe, Tetrahedron Lett. 1991, 32, 4863-4866 and Tetrahedron 1994, 50, 1419-1434; T. Doi, T. Takahashi, J. Org. Chem. 1991, 56, 3465-3467; M. Hirama, T. Gomibuchi, K. Fujiwara, Y. Sugiura, M. Uesugi, J. Am. Chem. Soc. 1991, 113, 9851-9853; M. Hirama, M. Tokuda, K. Fujiwara, Synlett 1991, 651-653; M. Tokuda, K. Fujiwara, T. Gomibuchi, M. Hirama, M. Uesugi, Y. Sugiura, Tetrahedron Lett. 1993, 34, 669-672; Y. Matsumoto, Y. Kuwatani, I. Ueda, Tetrahedron Lett. 1995, 36, 3197-3200; R. F. Cunico, S. K. Nair, Tetrahedron Lett. 1997, 38, 25-28; S. Caddick, S. Khan, N. J. Smith, D. M. Barr, V. M. Delisser, Tetrahedron Lett. 1997, 38, 5035-5036.
111. M. Hirama, K. Fujiwara, K. Shigematu, Y. Fukazawa, J. Am. Chem. Soc. 1989, 111, 4120-4122; ref. 40; P. A. Wender, M. J. Tebbe, Tetrahedron Lett. 1991, 32, 4863-4866 and Tetrahedron 1994, 50, 1419-1434; T. Doi, T. Takahashi, J. Org. Chem. 1991, 56, 3465-3467; M. Hirama, T. Gomibuchi, K. Fujiwara, Y. Sugiura, M. Uesugi, J. Am. Chem. Soc. 1991, 113, 9851-9853; M. Hirama, M. Tokuda, K. Fujiwara, Synlett 1991, 651-653; M. Tokuda, K. Fujiwara, T. Gomibuchi, M. Hirama, M. Uesugi, Y. Sugiura, Tetrahedron Lett. 1993, 34, 669-672; Y. Matsumoto, Y. Kuwatani, I. Ueda, Tetrahedron Lett. 1995, 36, 3197-3200; R. F. Cunico, S. K. Nair, Tetrahedron Lett. 1997, 38, 25-28; S. Caddick, S. Khan, N. J. Smith, D. M. Barr, V. M. Delisser, Tetrahedron Lett. 1997, 38, 5035-5036.
112. M. Hirama, K. Fujiwara, K. Shigematu, Y. Fukazawa, J. Am. Chem. Soc. 1989, 111, 4120-4122; ref. 40; P. A. Wender, M. J. Tebbe, Tetrahedron Lett. 1991, 32, 4863-4866 and Tetrahedron 1994, 50, 1419-1434; T. Doi, T. Takahashi, J. Org. Chem. 1991, 56, 3465-3467; M. Hirama, T. Gomibuchi, K. Fujiwara, Y. Sugiura, M. Uesugi, J. Am. Chem. Soc. 1991, 113, 9851-9853; M. Hirama, M. Tokuda, K. Fujiwara, Synlett 1991, 651-653; M. Tokuda, K. Fujiwara, T. Gomibuchi, M. Hirama, M. Uesugi, Y. Sugiura, Tetrahedron Lett. 1993, 34, 669-672; Y. Matsumoto, Y. Kuwatani, I. Ueda, Tetrahedron Lett. 1995, 36, 3197-3200; R. F. Cunico, S. K. Nair, Tetrahedron Lett. 1997, 38, 25-28; S. Caddick, S. Khan, N. J. Smith, D. M. Barr, V. M. Delisser, Tetrahedron Lett. 1997, 38, 5035-5036.
113. M. Eckhardt, R. Brückner, Liebigs Ann. / Recueil 1997, 947-959.
114. Method: J. E. McMurry, Chem. Rev. 1989, 89, 1513-1524; G. M. Robertson in Vol. 3 (Ed. G. Pattenden) of Comprehensive Organic Synthesis (Eds. B. M. Trost, I. Fleming), Pergamon Press, Oxford, 1991, 563-611; T. Lectka, in Active Metals (Ed. A. Fürstner), VCH, Weinheim, 1996, 85-131; A. Fürstner, B. Bogdanovic, Angew. Chem. 1996, 108, 2582-2609; Angew. Chem. Int. Ed. Engl. 1996, 35, 2442-2469.
115. Method: J. E. McMurry, Chem. Rev. 1989, 89, 1513-1524; G. M. Robertson in Vol. 3 (Ed. G. Pattenden) of Comprehensive Organic Synthesis (Eds. B. M. Trost, I. Fleming), Pergamon Press, Oxford, 1991, 563-611; T. Lectka, in Active Metals (Ed. A. Fürstner), VCH, Weinheim, 1996, 85-131; A. Fürstner, B. Bogdanovic, Angew. Chem. 1996, 108, 2582-2609; Angew. Chem. Int. Ed. Engl. 1996, 35, 2442-2469.
116. Method: J. E. McMurry, Chem. Rev. 1989, 89, 1513-1524; G. M. Robertson in Vol. 3 (Ed. G. Pattenden) of Comprehensive Organic Synthesis (Eds. B. M. Trost, I. Fleming), Pergamon Press, Oxford, 1991, 563-611; T. Lectka, in Active Metals (Ed. A. Fürstner), VCH, Weinheim, 1996, 85-131; A. Fürstner, B. Bogdanovic, Angew. Chem. 1996, 108, 2582-2609; Angew. Chem. Int. Ed. Engl. 1996, 35, 2442-2469.
117. Method: J. E. McMurry, Chem. Rev. 1989, 89, 1513-1524; G. M. Robertson in Vol. 3 (Ed. G. Pattenden) of Comprehensive Organic Synthesis (Eds. B. M. Trost, I. Fleming), Pergamon Press, Oxford, 1991, 563-611; T. Lectka, in Active Metals (Ed. A. Fürstner), VCH, Weinheim, 1996, 85-131; A. Fürstner, B. Bogdanovic, Angew. Chem. 1996, 108, 2582-2609; Angew. Chem. Int. Ed. Engl. 1996, 35, 2442-2469.
118. Method: J. E. McMurry, Chem. Rev. 1989, 89, 1513-1524; G. M. Robertson in Vol. 3 (Ed. G. Pattenden) of Comprehensive Organic Synthesis (Eds. B. M. Trost, I. Fleming), Pergamon Press, Oxford, 1991, 563-611; T. Lectka, in Active Metals (Ed. A. Fürstner), VCH, Weinheim, 1996, 85-131; A. Fürstner, B. Bogdanovic, Angew. Chem. 1996, 108, 2582-2609; Angew. Chem. Int. Ed. Engl. 1996, 35, 2442-2469.
119. F. Ferri, R. Brückner, unpublished.
120. M. Eckhardt, R. Brückner, Angew. Chem. 1996, 108, 1185-1188; Angew. Chem. Int. Ed. Engl. 1996, 35, 1093-1096.
121. M. Eckhardt, R. Brückner, Angew. Chem. 1996, 108, 1185-1188; Angew. Chem. Int. Ed. Engl. 1996, 35, 1093-1096.
122. F. Ferri, R. Brückner, Liebigs Ann. / Recueil 1997, 961-965.
123. Method: K. B. Sharpless in I. Ojima, "Catalytic Asymmetric Synthesis", VCH, Weinheim 1993, 227-272.
124. Method: I. Fleming, Chemtracts: Org. Chem. 1996, 9, 1-64; G. R. Jones, Y. Landais, Tetrahedron 1996, 52, 7599-7662.
125. Method: I. Fleming, Chemtracts: Org. Chem. 1996, 9, 1-64; G. R. Jones, Y. Landais, Tetrahedron 1996, 52, 7599-7662.
126. M. C. Carreño, J. L. Garća Ruano, M. Garrido, M. P. Ruiz, G. Solladié, Tetrahedron Lett. 1990, 31, 6653-6656.
127. R. Brünjes, U. Tilstam, E. Winterfeldt, Chem. Ber. 1991, 124, 1677-1678; Z. G. Hajos, D. R. Parrish, Org. Synth. Coll. Vol. 7, 1990, 363-368 and K. Matcheva, M. Beckmann, D. Schomburg, E. Winterfeldt, Synthesis 1989, 814-817.
128. R. Brünjes, U. Tilstam, E. Winterfeldt, Chem. Ber. 1991, 124, 1677-1678; Z. G. Hajos, D. R. Parrish, Org. Synth. Coll. Vol. 7, 1990, 363-368 and K. Matcheva, M. Beckmann, D. Schomburg, E. Winterfeldt, Synthesis 1989, 814-817.
129. R. Brünjes, U. Tilstam, E. Winterfeldt, Chem. Ber. 1991, 124, 1677-1678; Z. G. Hajos, D. R. Parrish, Org. Synth. Coll. Vol. 7, 1990, 363-368 and K. Matcheva, M. Beckmann, D. Schomburg, E. Winterfeldt, Synthesis 1989, 814-817.
130. M. C. Witschel, H. J. Bestmann, Synthesis 1997, 107-112.
131. O. Gebauer, R. Brückner, Liebigs Ann. 1996, 1559-1563.
132. O. Gebauer, R. Brückner, unpublished.
133. S. V. Ley, H. W. M. Priepke, S. L. Warriner, Angew. Chem. 1994, 106, 2410-2412; Angew. Chem. Int. Ed. Engl. 1994, 33, 2288-2290; S. V. Ley, H. W. M. Priepke, Angew. Chem. 1994, 106, 2412-2414; Angew. Chem. Int. Ed. Engl. 1994, 33, 2290-2292.
134. S. V. Ley, H. W. M. Priepke, S. L. Warriner, Angew. Chem. 1994, 106, 2410-2412; Angew. Chem. Int. Ed. Engl. 1994, 33, 2288-2290; S. V. Ley, H. W. M. Priepke, Angew. Chem. 1994, 106, 2412-2414; Angew. Chem. Int. Ed. Engl. 1994, 33, 2290-2292.
135. S. V. Ley, H. W. M. Priepke, S. L. Warriner, Angew. Chem. 1994, 106, 2410-2412; Angew. Chem. Int. Ed. Engl. 1994, 33, 2288-2290; S. V. Ley, H. W. M. Priepke, Angew. Chem. 1994, 106, 2412-2414; Angew. Chem. Int. Ed. Engl. 1994, 33, 2290-2292.
136. S. V. Ley, H. W. M. Priepke, S. L. Warriner, Angew. Chem. 1994, 106, 2410-2412; Angew. Chem. Int. Ed. Engl. 1994, 33, 2288-2290; S. V. Ley, H. W. M. Priepke, Angew. Chem. 1994, 106, 2412-2414; Angew. Chem. Int. Ed. Engl. 1994, 33, 2290-2292.
137. M. Eckhardt, R, Brückner, unpublished.
138. Reagent: K. Tamao, A. Kawachi, Y. Ito, J.66 Am. Chem. Soc. 1992, 114, 3989-3990.