A second-generation radical-based synthesis of (+)-7- deoxypancratistatin

Journal of Organic Chemistry

Volumn 63, Issue 25, 1998, Pages 9164-9165

  Keck, Gary E ^a   Wager, Travis T ^a   McHardy, Stanton F ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

7 DEOXYPANCRATISTATIN; ALKALOID; AZIRIDINYLIMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 0032509231     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981890s     Document Type: Article

References (25)

1. For syntheses of pancratistatin see: (a) Danishefsky, S.; Lee, J. Y. J. Am. Chem. Soc. 1989, 111, 4829. (b) Hudlicky, T.; Tian, X.; Königsberger, K.; Maurya, R.; Rouden, J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752. (c) Trost, B. M.; Pulley, S. R. J. Am. Chem. Soc. 1995, 117, 10143. (d) Doyle, T. J.; Hendrix, M.; VanDerveer, D.; Javanmard, S.; Haseltine, J. Tetrahedron, 1997, 53, 11153. (e) Magnus, P.; Sebhat, I. K. J. Am. Chem. Soc. 1998, 120, 5341. For syntheses of 7-deoxypancratistatin see: (f) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2977. (g) Paulsen, H.; Stubbe, M. Liebigs Ann. Chem. 1983, 535. (h) Tian, X.; Maurya, R.; Königsberger, K.; Hudlicky, T. Synlett 1995, 1125. (i) Chida, N.; Iitsuoka, M.; Yamamoto, Y.; Ohtsuka, M.; Ogawa, S. Heterocycles 1996, 43, 1385. For a review of synthetic work in this area, see: Polt, R. In Organic Synthesis: Theory and Application; Hudlicky, T., Ed.; JAI Press: Greenwich, 1996; Vol. 3, p 109.
2. For syntheses of pancratistatin see: (a) Danishefsky, S.; Lee, J. Y. J. Am. Chem. Soc. 1989, 111, 4829. (b) Hudlicky, T.; Tian, X.; Königsberger, K.; Maurya, R.; Rouden, J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752. (c) Trost, B. M.; Pulley, S. R. J. Am. Chem. Soc. 1995, 117, 10143. (d) Doyle, T. J.; Hendrix, M.; VanDerveer, D.; Javanmard, S.; Haseltine, J. Tetrahedron, 1997, 53, 11153. (e) Magnus, P.; Sebhat, I. K. J. Am. Chem. Soc. 1998, 120, 5341. For syntheses of 7-deoxypancratistatin see: (f) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2977. (g) Paulsen, H.; Stubbe, M. Liebigs Ann. Chem. 1983, 535. (h) Tian, X.; Maurya, R.; Königsberger, K.; Hudlicky, T. Synlett 1995, 1125. (i) Chida, N.; Iitsuoka, M.; Yamamoto, Y.; Ohtsuka, M.; Ogawa, S. Heterocycles 1996, 43, 1385. For a review of synthetic work in this area, see: Polt, R. In Organic Synthesis: Theory and Application; Hudlicky, T., Ed.; JAI Press: Greenwich, 1996; Vol. 3, p 109.
3. For syntheses of pancratistatin see: (a) Danishefsky, S.; Lee, J. Y. J. Am. Chem. Soc. 1989, 111, 4829. (b) Hudlicky, T.; Tian, X.; Königsberger, K.; Maurya, R.; Rouden, J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752. (c) Trost, B. M.; Pulley, S. R. J. Am. Chem. Soc. 1995, 117, 10143. (d) Doyle, T. J.; Hendrix, M.; VanDerveer, D.; Javanmard, S.; Haseltine, J. Tetrahedron, 1997, 53, 11153. (e) Magnus, P.; Sebhat, I. K. J. Am. Chem. Soc. 1998, 120, 5341. For syntheses of 7-deoxypancratistatin see: (f) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2977. (g) Paulsen, H.; Stubbe, M. Liebigs Ann. Chem. 1983, 535. (h) Tian, X.; Maurya, R.; Königsberger, K.; Hudlicky, T. Synlett 1995, 1125. (i) Chida, N.; Iitsuoka, M.; Yamamoto, Y.; Ohtsuka, M.; Ogawa, S. Heterocycles 1996, 43, 1385. For a review of synthetic work in this area, see: Polt, R. In Organic Synthesis: Theory and Application; Hudlicky, T., Ed.; JAI Press: Greenwich, 1996; Vol. 3, p 109.
4. For syntheses of pancratistatin see: (a) Danishefsky, S.; Lee, J. Y. J. Am. Chem. Soc. 1989, 111, 4829. (b) Hudlicky, T.; Tian, X.; Königsberger, K.; Maurya, R.; Rouden, J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752. (c) Trost, B. M.; Pulley, S. R. J. Am. Chem. Soc. 1995, 117, 10143. (d) Doyle, T. J.; Hendrix, M.; VanDerveer, D.; Javanmard, S.; Haseltine, J. Tetrahedron, 1997, 53, 11153. (e) Magnus, P.; Sebhat, I. K. J. Am. Chem. Soc. 1998, 120, 5341. For syntheses of 7-deoxypancratistatin see: (f) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2977. (g) Paulsen, H.; Stubbe, M. Liebigs Ann. Chem. 1983, 535. (h) Tian, X.; Maurya, R.; Königsberger, K.; Hudlicky, T. Synlett 1995, 1125. (i) Chida, N.; Iitsuoka, M.; Yamamoto, Y.; Ohtsuka, M.; Ogawa, S. Heterocycles 1996, 43, 1385. For a review of synthetic work in this area, see: Polt, R. In Organic Synthesis: Theory and Application; Hudlicky, T., Ed.; JAI Press: Greenwich, 1996; Vol. 3, p 109.
5. For syntheses of pancratistatin see: (a) Danishefsky, S.; Lee, J. Y. J. Am. Chem. Soc. 1989, 111, 4829. (b) Hudlicky, T.; Tian, X.; Königsberger, K.; Maurya, R.; Rouden, J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752. (c) Trost, B. M.; Pulley, S. R. J. Am. Chem. Soc. 1995, 117, 10143. (d) Doyle, T. J.; Hendrix, M.; VanDerveer, D.; Javanmard, S.; Haseltine, J. Tetrahedron, 1997, 53, 11153. (e) Magnus, P.; Sebhat, I. K. J. Am. Chem. Soc. 1998, 120, 5341. For syntheses of 7-deoxypancratistatin see: (f) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2977. (g) Paulsen, H.; Stubbe, M. Liebigs Ann. Chem. 1983, 535. (h) Tian, X.; Maurya, R.; Königsberger, K.; Hudlicky, T. Synlett 1995, 1125. (i) Chida, N.; Iitsuoka, M.; Yamamoto, Y.; Ohtsuka, M.; Ogawa, S. Heterocycles 1996, 43, 1385. For a review of synthetic work in this area, see: Polt, R. In Organic Synthesis: Theory and Application; Hudlicky, T., Ed.; JAI Press: Greenwich, 1996; Vol. 3, p 109.
6. For syntheses of pancratistatin see: (a) Danishefsky, S.; Lee, J. Y. J. Am. Chem. Soc. 1989, 111, 4829. (b) Hudlicky, T.; Tian, X.; Königsberger, K.; Maurya, R.; Rouden, J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752. (c) Trost, B. M.; Pulley, S. R. J. Am. Chem. Soc. 1995, 117, 10143. (d) Doyle, T. J.; Hendrix, M.; VanDerveer, D.; Javanmard, S.; Haseltine, J. Tetrahedron, 1997, 53, 11153. (e) Magnus, P.; Sebhat, I. K. J. Am. Chem. Soc. 1998, 120, 5341. For syntheses of 7-deoxypancratistatin see: (f) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2977. (g) Paulsen, H.; Stubbe, M. Liebigs Ann. Chem. 1983, 535. (h) Tian, X.; Maurya, R.; Königsberger, K.; Hudlicky, T. Synlett 1995, 1125. (i) Chida, N.; Iitsuoka, M.; Yamamoto, Y.; Ohtsuka, M.; Ogawa, S. Heterocycles 1996, 43, 1385. For a review of synthetic work in this area, see: Polt, R. In Organic Synthesis: Theory and Application; Hudlicky, T., Ed.; JAI Press: Greenwich, 1996; Vol. 3, p 109.
7. For syntheses of pancratistatin see: (a) Danishefsky, S.; Lee, J. Y. J. Am. Chem. Soc. 1989, 111, 4829. (b) Hudlicky, T.; Tian, X.; Königsberger, K.; Maurya, R.; Rouden, J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752. (c) Trost, B. M.; Pulley, S. R. J. Am. Chem. Soc. 1995, 117, 10143. (d) Doyle, T. J.; Hendrix, M.; VanDerveer, D.; Javanmard, S.; Haseltine, J. Tetrahedron, 1997, 53, 11153. (e) Magnus, P.; Sebhat, I. K. J. Am. Chem. Soc. 1998, 120, 5341. For syntheses of 7-deoxypancratistatin see: (f) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2977. (g) Paulsen, H.; Stubbe, M. Liebigs Ann. Chem. 1983, 535. (h) Tian, X.; Maurya, R.; Königsberger, K.; Hudlicky, T. Synlett 1995, 1125. (i) Chida, N.; Iitsuoka, M.; Yamamoto, Y.; Ohtsuka, M.; Ogawa, S. Heterocycles 1996, 43, 1385. For a review of synthetic work in this area, see: Polt, R. In Organic Synthesis: Theory and Application; Hudlicky, T., Ed.; JAI Press: Greenwich, 1996; Vol. 3, p 109.
8. For syntheses of pancratistatin see: (a) Danishefsky, S.; Lee, J. Y. J. Am. Chem. Soc. 1989, 111, 4829. (b) Hudlicky, T.; Tian, X.; Königsberger, K.; Maurya, R.; Rouden, J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752. (c) Trost, B. M.; Pulley, S. R. J. Am. Chem. Soc. 1995, 117, 10143. (d) Doyle, T. J.; Hendrix, M.; VanDerveer, D.; Javanmard, S.; Haseltine, J. Tetrahedron, 1997, 53, 11153. (e) Magnus, P.; Sebhat, I. K. J. Am. Chem. Soc. 1998, 120, 5341. For syntheses of 7-deoxypancratistatin see: (f) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2977. (g) Paulsen, H.; Stubbe, M. Liebigs Ann. Chem. 1983, 535. (h) Tian, X.; Maurya, R.; Königsberger, K.; Hudlicky, T. Synlett 1995, 1125. (i) Chida, N.; Iitsuoka, M.; Yamamoto, Y.; Ohtsuka, M.; Ogawa, S. Heterocycles 1996, 43, 1385. For a review of synthetic work in this area, see: Polt, R. In Organic Synthesis: Theory and Application; Hudlicky, T., Ed.; JAI Press: Greenwich, 1996; Vol. 3, p 109.
9. For syntheses of pancratistatin see: (a) Danishefsky, S.; Lee, J. Y. J. Am. Chem. Soc. 1989, 111, 4829. (b) Hudlicky, T.; Tian, X.; Königsberger, K.; Maurya, R.; Rouden, J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752. (c) Trost, B. M.; Pulley, S. R. J. Am. Chem. Soc. 1995, 117, 10143. (d) Doyle, T. J.; Hendrix, M.; VanDerveer, D.; Javanmard, S.; Haseltine, J. Tetrahedron, 1997, 53, 11153. (e) Magnus, P.; Sebhat, I. K. J. Am. Chem. Soc. 1998, 120, 5341. For syntheses of 7-deoxypancratistatin see: (f) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2977. (g) Paulsen, H.; Stubbe, M. Liebigs Ann. Chem. 1983, 535. (h) Tian, X.; Maurya, R.; Königsberger, K.; Hudlicky, T. Synlett 1995, 1125. (i) Chida, N.; Iitsuoka, M.; Yamamoto, Y.; Ohtsuka, M.; Ogawa, S. Heterocycles 1996, 43, 1385. For a review of synthetic work in this area, see: Polt, R. In Organic Synthesis: Theory and Application; Hudlicky, T., Ed.; JAI Press: Greenwich, 1996; Vol. 3, p 109.
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