Synthesis of the South unit of cephalostatin. 7. Total syntheses of (+)- cephalostatin 7, (+)-cephalostatin 12, and (+)-ritterazine K

Journal of the American Chemical Society

Volumn 121, Issue 10, 1999, Pages 2071-2084

  Jeong, Jae Uk ^a   Guo, Chuangxing ^a   Fuchs, P L ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CEPHALOSTATIN 12; CEPHALOSTATIN 7; PYRAZINE DERIVATIVE; RITTERAZINE K; UNCLASSIFIED DRUG;

ARTICLE; DIMERIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0001678926     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9817141     Document Type: Article

References (56)

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2. Cephalostatin Synthesis. 15. Portions of this work have been communicated in Articles 6 and 9 of this series: Jeong, J. U.; Fuchs, P. L. Tetrahedron Lett. 1995, 36, 2431. Jeong, J. U.; Sutton, S. C.; Kim, S.; Fuchs, P. L. J. Am. Chem. Soc. 1995, 117, 10157. For additional syntheses of cephalostatin-related pyrazines, see: (a) Pan, Y.; Merriman, R. L.; Tanzer, L. R.; Fuchs, P. L. Bioorg. Med. Chem. Lett. 1992, 2, 967. (b) Heathcock, C. H.; Smith, S. C. J. Org. Chem. 1994, 59, 6828. (c) Kramer, A.; Ullmann, U.; Winterfeldt, E. J. Chem. Soc., Perkin Trans. 1 1993, 2865. (d) Ganesan, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 611. (e) Drogemuller, M.; Jantelat, R.; Winterfelt, E. Angew. Chem., Int. Ed. Engl. 1996, 35, 1572. (f) Guo, C.; Bhandaru, S.; Fuchs, P. L.; Boyd, M. R. J. Am. Chem. Soc. 1996, 118, 10672. (g) LaCour, T. G.; Guo, C.; Bhandaru, S.; Boyd, M. R.; Fuchs, P. L. J. Am. Chem. Soc. 1998, 120, 692. (h) Drögemüller, M.; Flessner, T.; Jaulelat, R.; Scholz, U.; Winterfeldt, E. Eur. J. Org. Chem. 1998, 2811.
3. Cephalostatin Synthesis. 15. Portions of this work have been communicated in Articles 6 and 9 of this series: Jeong, J. U.; Fuchs, P. L. Tetrahedron Lett. 1995, 36, 2431. Jeong, J. U.; Sutton, S. C.; Kim, S.; Fuchs, P. L. J. Am. Chem. Soc. 1995, 117, 10157. For additional syntheses of cephalostatin-related pyrazines, see: (a) Pan, Y.; Merriman, R. L.; Tanzer, L. R.; Fuchs, P. L. Bioorg. Med. Chem. Lett. 1992, 2, 967. (b) Heathcock, C. H.; Smith, S. C. J. Org. Chem. 1994, 59, 6828. (c) Kramer, A.; Ullmann, U.; Winterfeldt, E. J. Chem. Soc., Perkin Trans. 1 1993, 2865. (d) Ganesan, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 611. (e) Drogemuller, M.; Jantelat, R.; Winterfelt, E. Angew. Chem., Int. Ed. Engl. 1996, 35, 1572. (f) Guo, C.; Bhandaru, S.; Fuchs, P. L.; Boyd, M. R. J. Am. Chem. Soc. 1996, 118, 10672. (g) LaCour, T. G.; Guo, C.; Bhandaru, S.; Boyd, M. R.; Fuchs, P. L. J. Am. Chem. Soc. 1998, 120, 692. (h) Drögemüller, M.; Flessner, T.; Jaulelat, R.; Scholz, U.; Winterfeldt, E. Eur. J. Org. Chem. 1998, 2811.
4. Cephalostatin Synthesis. 15. Portions of this work have been communicated in Articles 6 and 9 of this series: Jeong, J. U.; Fuchs, P. L. Tetrahedron Lett. 1995, 36, 2431. Jeong, J. U.; Sutton, S. C.; Kim, S.; Fuchs, P. L. J. Am. Chem. Soc. 1995, 117, 10157. For additional syntheses of cephalostatin-related pyrazines, see: (a) Pan, Y.; Merriman, R. L.; Tanzer, L. R.; Fuchs, P. L. Bioorg. Med. Chem. Lett. 1992, 2, 967. (b) Heathcock, C. H.; Smith, S. C. J. Org. Chem. 1994, 59, 6828. (c) Kramer, A.; Ullmann, U.; Winterfeldt, E. J. Chem. Soc., Perkin Trans. 1 1993, 2865. (d) Ganesan, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 611. (e) Drogemuller, M.; Jantelat, R.; Winterfelt, E. Angew. Chem., Int. Ed. Engl. 1996, 35, 1572. (f) Guo, C.; Bhandaru, S.; Fuchs, P. L.; Boyd, M. R. J. Am. Chem. Soc. 1996, 118, 10672. (g) LaCour, T. G.; Guo, C.; Bhandaru, S.; Boyd, M. R.; Fuchs, P. L. J. Am. Chem. Soc. 1998, 120, 692. (h) Drögemüller, M.; Flessner, T.; Jaulelat, R.; Scholz, U.; Winterfeldt, E. Eur. J. Org. Chem. 1998, 2811.
5. Cephalostatin Synthesis. 15. Portions of this work have been communicated in Articles 6 and 9 of this series: Jeong, J. U.; Fuchs, P. L. Tetrahedron Lett. 1995, 36, 2431. Jeong, J. U.; Sutton, S. C.; Kim, S.; Fuchs, P. L. J. Am. Chem. Soc. 1995, 117, 10157. For additional syntheses of cephalostatin-related pyrazines, see: (a) Pan, Y.; Merriman, R. L.; Tanzer, L. R.; Fuchs, P. L. Bioorg. Med. Chem. Lett. 1992, 2, 967. (b) Heathcock, C. H.; Smith, S. C. J. Org. Chem. 1994, 59, 6828. (c) Kramer, A.; Ullmann, U.; Winterfeldt, E. J. Chem. Soc., Perkin Trans. 1 1993, 2865. (d) Ganesan, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 611. (e) Drogemuller, M.; Jantelat, R.; Winterfelt, E. Angew. Chem., Int. Ed. Engl. 1996, 35, 1572. (f) Guo, C.; Bhandaru, S.; Fuchs, P. L.; Boyd, M. R. J. Am. Chem. Soc. 1996, 118, 10672. (g) LaCour, T. G.; Guo, C.; Bhandaru, S.; Boyd, M. R.; Fuchs, P. L. J. Am. Chem. Soc. 1998, 120, 692. (h) Drögemüller, M.; Flessner, T.; Jaulelat, R.; Scholz, U.; Winterfeldt, E. Eur. J. Org. Chem. 1998, 2811.
6. Cephalostatin Synthesis. 15. Portions of this work have been communicated in Articles 6 and 9 of this series: Jeong, J. U.; Fuchs, P. L. Tetrahedron Lett. 1995, 36, 2431. Jeong, J. U.; Sutton, S. C.; Kim, S.; Fuchs, P. L. J. Am. Chem. Soc. 1995, 117, 10157. For additional syntheses of cephalostatin-related pyrazines, see: (a) Pan, Y.; Merriman, R. L.; Tanzer, L. R.; Fuchs, P. L. Bioorg. Med. Chem. Lett. 1992, 2, 967. (b) Heathcock, C. H.; Smith, S. C. J. Org. Chem. 1994, 59, 6828. (c) Kramer, A.; Ullmann, U.; Winterfeldt, E. J. Chem. Soc., Perkin Trans. 1 1993, 2865. (d) Ganesan, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 611. (e) Drogemuller, M.; Jantelat, R.; Winterfelt, E. Angew. Chem., Int. Ed. Engl. 1996, 35, 1572. (f) Guo, C.; Bhandaru, S.; Fuchs, P. L.; Boyd, M. R. J. Am. Chem. Soc. 1996, 118, 10672. (g) LaCour, T. G.; Guo, C.; Bhandaru, S.; Boyd, M. R.; Fuchs, P. L. J. Am. Chem. Soc. 1998, 120, 692. (h) Drögemüller, M.; Flessner, T.; Jaulelat, R.; Scholz, U.; Winterfeldt, E. Eur. J. Org. Chem. 1998, 2811.
7. Cephalostatin Synthesis. 15. Portions of this work have been communicated in Articles 6 and 9 of this series: Jeong, J. U.; Fuchs, P. L. Tetrahedron Lett. 1995, 36, 2431. Jeong, J. U.; Sutton, S. C.; Kim, S.; Fuchs, P. L. J. Am. Chem. Soc. 1995, 117, 10157. For additional syntheses of cephalostatin-related pyrazines, see: (a) Pan, Y.; Merriman, R. L.; Tanzer, L. R.; Fuchs, P. L. Bioorg. Med. Chem. Lett. 1992, 2, 967. (b) Heathcock, C. H.; Smith, S. C. J. Org. Chem. 1994, 59, 6828. (c) Kramer, A.; Ullmann, U.; Winterfeldt, E. J. Chem. Soc., Perkin Trans. 1 1993, 2865. (d) Ganesan, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 611. (e) Drogemuller, M.; Jantelat, R.; Winterfelt, E. Angew. Chem., Int. Ed. Engl. 1996, 35, 1572. (f) Guo, C.; Bhandaru, S.; Fuchs, P. L.; Boyd, M. R. J. Am. Chem. Soc. 1996, 118, 10672. (g) LaCour, T. G.; Guo, C.; Bhandaru, S.; Boyd, M. R.; Fuchs, P. L. J. Am. Chem. Soc. 1998, 120, 692. (h) Drögemüller, M.; Flessner, T.; Jaulelat, R.; Scholz, U.; Winterfeldt, E. Eur. J. Org. Chem. 1998, 2811.
8. Cephalostatin Synthesis. 15. Portions of this work have been communicated in Articles 6 and 9 of this series: Jeong, J. U.; Fuchs, P. L. Tetrahedron Lett. 1995, 36, 2431. Jeong, J. U.; Sutton, S. C.; Kim, S.; Fuchs, P. L. J. Am. Chem. Soc. 1995, 117, 10157. For additional syntheses of cephalostatin-related pyrazines, see: (a) Pan, Y.; Merriman, R. L.; Tanzer, L. R.; Fuchs, P. L. Bioorg. Med. Chem. Lett. 1992, 2, 967. (b) Heathcock, C. H.; Smith, S. C. J. Org. Chem. 1994, 59, 6828. (c) Kramer, A.; Ullmann, U.; Winterfeldt, E. J. Chem. Soc., Perkin Trans. 1 1993, 2865. (d) Ganesan, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 611. (e) Drogemuller, M.; Jantelat, R.; Winterfelt, E. Angew. Chem., Int. Ed. Engl. 1996, 35, 1572. (f) Guo, C.; Bhandaru, S.; Fuchs, P. L.; Boyd, M. R. J. Am. Chem. Soc. 1996, 118, 10672. (g) LaCour, T. G.; Guo, C.; Bhandaru, S.; Boyd, M. R.; Fuchs, P. L. J. Am. Chem. Soc. 1998, 120, 692. (h) Drögemüller, M.; Flessner, T.; Jaulelat, R.; Scholz, U.; Winterfeldt, E. Eur. J. Org. Chem. 1998, 2811.
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