Total synthesis of zaragozic acid A (squalestatin S1). Degradation to a relay compound and reassembly of the natural product

Journal of Organic Chemistry

Volumn 61, Issue 26, 1996, Pages 9115-9125

  Stoermer, Doris ^a   Caron, Stéphane ^a   Heathcock, Clayton H ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ZARAGOZIC ACID A;

ARTICLE; DRUG SYNTHESIS; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030460962     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961533m     Document Type: Article

References (52)

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12. For other zaragozic acid total syntheses, see: (a) Carreria, E. M.; Du Bois, J. J. Am. Chem. Soc. 1994, 116, 10825. (b) Carreira, E. M.; Du Bois, J. J. Am. Chem. Soc. 1995, 117, 8106. (c) Nicolaou, K. C.; Yue, E. W.; Yoshimitsu, N.; De Riccardis, F.; Nadin, A.; Leresche, J. E.; La Greca, S.; Yang, Z. Angew. Chem., Int. Ed. Engl. 1994, 33, 2184. (d) Nicolaou, K. C.; Nadin, A.; Leresche, J. E.; La Greca, S.; Tsuri, T.; Yue, E. W.; Yang, Z. Angew. Chem., Int. Ed. Engl. 1994, 33, 2187. (e) Nicolaou, K. C.; Nadin, A.; Leresche, J. E.; Yue, E. W.; La Greca, S. Angew. Chem., Int. Ed. Engl. 1994, 33, 2190. (f) Nicolaou, K. C.; Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F. Chem. Eur. J. 1995, 1, 467. (g) Evans, D. A.; Barrow, J. C.; Leighton, J. L.; Robichaud, A. J.; Sefkow, M. J. Am. Chem. Soc. 1994, 116, 12111. For reviews of the syntheses of the zaragozic acids, see: (h) Koert, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 773. (i) Nadin, A.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1623.
13. For other zaragozic acid total syntheses, see: (a) Carreria, E. M.; Du Bois, J. J. Am. Chem. Soc. 1994, 116, 10825. (b) Carreira, E. M.; Du Bois, J. J. Am. Chem. Soc. 1995, 117, 8106. (c) Nicolaou, K. C.; Yue, E. W.; Yoshimitsu, N.; De Riccardis, F.; Nadin, A.; Leresche, J. E.; La Greca, S.; Yang, Z. Angew. Chem., Int. Ed. Engl. 1994, 33, 2184. (d) Nicolaou, K. C.; Nadin, A.; Leresche, J. E.; La Greca, S.; Tsuri, T.; Yue, E. W.; Yang, Z. Angew. Chem., Int. Ed. Engl. 1994, 33, 2187. (e) Nicolaou, K. C.; Nadin, A.; Leresche, J. E.; Yue, E. W.; La Greca, S. Angew. Chem., Int. Ed. Engl. 1994, 33, 2190. (f) Nicolaou, K. C.; Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F. Chem. Eur. J. 1995, 1, 467. (g) Evans, D. A.; Barrow, J. C.; Leighton, J. L.; Robichaud, A. J.; Sefkow, M. J. Am. Chem. Soc. 1994, 116, 12111. For reviews of the syntheses of the zaragozic acids, see: (h) Koert, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 773. (i) Nadin, A.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1623.
14. For other zaragozic acid total syntheses, see: (a) Carreria, E. M.; Du Bois, J. J. Am. Chem. Soc. 1994, 116, 10825. (b) Carreira, E. M.; Du Bois, J. J. Am. Chem. Soc. 1995, 117, 8106. (c) Nicolaou, K. C.; Yue, E. W.; Yoshimitsu, N.; De Riccardis, F.; Nadin, A.; Leresche, J. E.; La Greca, S.; Yang, Z. Angew. Chem., Int. Ed. Engl. 1994, 33, 2184. (d) Nicolaou, K. C.; Nadin, A.; Leresche, J. E.; La Greca, S.; Tsuri, T.; Yue, E. W.; Yang, Z. Angew. Chem., Int. Ed. Engl. 1994, 33, 2187. (e) Nicolaou, K. C.; Nadin, A.; Leresche, J. E.; Yue, E. W.; La Greca, S. Angew. Chem., Int. Ed. Engl. 1994, 33, 2190. (f) Nicolaou, K. C.; Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F. Chem. Eur. J. 1995, 1, 467. (g) Evans, D. A.; Barrow, J. C.; Leighton, J. L.; Robichaud, A. J.; Sefkow, M. J. Am. Chem. Soc. 1994, 116, 12111. For reviews of the syntheses of the zaragozic acids, see: (h) Koert, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 773. (i) Nadin, A.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1623.
15. For other zaragozic acid total syntheses, see: (a) Carreria, E. M.; Du Bois, J. J. Am. Chem. Soc. 1994, 116, 10825. (b) Carreira, E. M.; Du Bois, J. J. Am. Chem. Soc. 1995, 117, 8106. (c) Nicolaou, K. C.; Yue, E. W.; Yoshimitsu, N.; De Riccardis, F.; Nadin, A.; Leresche, J. E.; La Greca, S.; Yang, Z. Angew. Chem., Int. Ed. Engl. 1994, 33, 2184. (d) Nicolaou, K. C.; Nadin, A.; Leresche, J. E.; La Greca, S.; Tsuri, T.; Yue, E. W.; Yang, Z. Angew. Chem., Int. Ed. Engl. 1994, 33, 2187. (e) Nicolaou, K. C.; Nadin, A.; Leresche, J. E.; Yue, E. W.; La Greca, S. Angew. Chem., Int. Ed. Engl. 1994, 33, 2190. (f) Nicolaou, K. C.; Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F. Chem. Eur. J. 1995, 1, 467. (g) Evans, D. A.; Barrow, J. C.; Leighton, J. L.; Robichaud, A. J.; Sefkow, M. J. Am. Chem. Soc. 1994, 116, 12111. For reviews of the syntheses of the zaragozic acids, see: (h) Koert, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 773. (i) Nadin, A.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1623.
16. For other zaragozic acid total syntheses, see: (a) Carreria, E. M.; Du Bois, J. J. Am. Chem. Soc. 1994, 116, 10825. (b) Carreira, E. M.; Du Bois, J. J. Am. Chem. Soc. 1995, 117, 8106. (c) Nicolaou, K. C.; Yue, E. W.; Yoshimitsu, N.; De Riccardis, F.; Nadin, A.; Leresche, J. E.; La Greca, S.; Yang, Z. Angew. Chem., Int. Ed. Engl. 1994, 33, 2184. (d) Nicolaou, K. C.; Nadin, A.; Leresche, J. E.; La Greca, S.; Tsuri, T.; Yue, E. W.; Yang, Z. Angew. Chem., Int. Ed. Engl. 1994, 33, 2187. (e) Nicolaou, K. C.; Nadin, A.; Leresche, J. E.; Yue, E. W.; La Greca, S. Angew. Chem., Int. Ed. Engl. 1994, 33, 2190. (f) Nicolaou, K. C.; Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F. Chem. Eur. J. 1995, 1, 467. (g) Evans, D. A.; Barrow, J. C.; Leighton, J. L.; Robichaud, A. J.; Sefkow, M. J. Am. Chem. Soc. 1994, 116, 12111. For reviews of the syntheses of the zaragozic acids, see: (h) Koert, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 773. (i) Nadin, A.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1623.
17. For other zaragozic acid total syntheses, see: (a) Carreria, E. M.; Du Bois, J. J. Am. Chem. Soc. 1994, 116, 10825. (b) Carreira, E. M.; Du Bois, J. J. Am. Chem. Soc. 1995, 117, 8106. (c) Nicolaou, K. C.; Yue, E. W.; Yoshimitsu, N.; De Riccardis, F.; Nadin, A.; Leresche, J. E.; La Greca, S.; Yang, Z. Angew. Chem., Int. Ed. Engl. 1994, 33, 2184. (d) Nicolaou, K. C.; Nadin, A.; Leresche, J. E.; La Greca, S.; Tsuri, T.; Yue, E. W.; Yang, Z. Angew. Chem., Int. Ed. Engl. 1994, 33, 2187. (e) Nicolaou, K. C.; Nadin, A.; Leresche, J. E.; Yue, E. W.; La Greca, S. Angew. Chem., Int. Ed. Engl. 1994, 33, 2190. (f) Nicolaou, K. C.; Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F. Chem. Eur. J. 1995, 1, 467. (g) Evans, D. A.; Barrow, J. C.; Leighton, J. L.; Robichaud, A. J.; Sefkow, M. J. Am. Chem. Soc. 1994, 116, 12111. For reviews of the syntheses of the zaragozic acids, see: (h) Koert, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 773. (i) Nadin, A.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1623.
18. For other zaragozic acid total syntheses, see: (a) Carreria, E. M.; Du Bois, J. J. Am. Chem. Soc. 1994, 116, 10825. (b) Carreira, E. M.; Du Bois, J. J. Am. Chem. Soc. 1995, 117, 8106. (c) Nicolaou, K. C.; Yue, E. W.; Yoshimitsu, N.; De Riccardis, F.; Nadin, A.; Leresche, J. E.; La Greca, S.; Yang, Z. Angew. Chem., Int. Ed. Engl. 1994, 33, 2184. (d) Nicolaou, K. C.; Nadin, A.; Leresche, J. E.; La Greca, S.; Tsuri, T.; Yue, E. W.; Yang, Z. Angew. Chem., Int. Ed. Engl. 1994, 33, 2187. (e) Nicolaou, K. C.; Nadin, A.; Leresche, J. E.; Yue, E. W.; La Greca, S. Angew. Chem., Int. Ed. Engl. 1994, 33, 2190. (f) Nicolaou, K. C.; Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F. Chem. Eur. J. 1995, 1, 467. (g) Evans, D. A.; Barrow, J. C.; Leighton, J. L.; Robichaud, A. J.; Sefkow, M. J. Am. Chem. Soc. 1994, 116, 12111. For reviews of the syntheses of the zaragozic acids, see: (h) Koert, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 773. (i) Nadin, A.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1623.
19. For other zaragozic acid total syntheses, see: (a) Carreria, E. M.; Du Bois, J. J. Am. Chem. Soc. 1994, 116, 10825. (b) Carreira, E. M.; Du Bois, J. J. Am. Chem. Soc. 1995, 117, 8106. (c) Nicolaou, K. C.; Yue, E. W.; Yoshimitsu, N.; De Riccardis, F.; Nadin, A.; Leresche, J. E.; La Greca, S.; Yang, Z. Angew. Chem., Int. Ed. Engl. 1994, 33, 2184. (d) Nicolaou, K. C.; Nadin, A.; Leresche, J. E.; La Greca, S.; Tsuri, T.; Yue, E. W.; Yang, Z. Angew. Chem., Int. Ed. Engl. 1994, 33, 2187. (e) Nicolaou, K. C.; Nadin, A.; Leresche, J. E.; Yue, E. W.; La Greca, S. Angew. Chem., Int. Ed. Engl. 1994, 33, 2190. (f) Nicolaou, K. C.; Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F. Chem. Eur. J. 1995, 1, 467. (g) Evans, D. A.; Barrow, J. C.; Leighton, J. L.; Robichaud, A. J.; Sefkow, M. J. Am. Chem. Soc. 1994, 116, 12111. For reviews of the syntheses of the zaragozic acids, see: (h) Koert, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 773. (i) Nadin, A.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1623.
20. For other zaragozic acid total syntheses, see: (a) Carreria, E. M.; Du Bois, J. J. Am. Chem. Soc. 1994, 116, 10825. (b) Carreira, E. M.; Du Bois, J. J. Am. Chem. Soc. 1995, 117, 8106. (c) Nicolaou, K. C.; Yue, E. W.; Yoshimitsu, N.; De Riccardis, F.; Nadin, A.; Leresche, J. E.; La Greca, S.; Yang, Z. Angew. Chem., Int. Ed. Engl. 1994, 33, 2184. (d) Nicolaou, K. C.; Nadin, A.; Leresche, J. E.; La Greca, S.; Tsuri, T.; Yue, E. W.; Yang, Z. Angew. Chem., Int. Ed. Engl. 1994, 33, 2187. (e) Nicolaou, K. C.; Nadin, A.; Leresche, J. E.; Yue, E. W.; La Greca, S. Angew. Chem., Int. Ed. Engl. 1994, 33, 2190. (f) Nicolaou, K. C.; Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F. Chem. Eur. J. 1995, 1, 467. (g) Evans, D. A.; Barrow, J. C.; Leighton, J. L.; Robichaud, A. J.; Sefkow, M. J. Am. Chem. Soc. 1994, 116, 12111. For reviews of the syntheses of the zaragozic acids, see: (h) Koert, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 773. (i) Nadin, A.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1623.
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