A formal total synthesis of (-)-FR901483, using a tandem cationic aza-Cope rearrangement/Mannich cyclization approach

Journal of Organic Chemistry

Volumn 70, Issue 3, 2005, Pages 907-916

  Brummond, Kay M ^a   Hong, Sang Phyo ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; OXYGEN; REACTION KINETICS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); ZINC COMPOUNDS;

AZA-COPE REARRANGEMENT; AZASPIRANE; IMMUNOSUPPRESSANTS; MANNICH CYCLIZATION REACTION;

ADDITIVES;

ALDEHYDE; AZASPIRANE; FR 901483; IMMUNOSUPPRESSIVE AGENT; PHENYLALANINE; UNCLASSIFIED DRUG; ZINC CHLORIDE;

ALDOL REACTION; ARTICLE; COPE REARRANGEMENT; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; EPIMERIZATION; MANNICH REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

AZA COMPOUNDS; CATIONS; CYCLIZATION; IMMUNOSUPPRESSIVE AGENTS; ORGANOPHOSPHORUS COMPOUNDS; STEREOISOMERISM;

EID: 13244252396     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0483567     Document Type: Article

References (42)

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8. For approaches to FR901483 and its analogues, see: (f) Quirante, J.; Escolano, C.; Massot, M.; Bonjoch, J. Tetrahedron 1997, 53, 1391. (g) Yamazaki, N.; Suzuki, H.; Kibayashi, C. J. Org. Chem. 1997, 62, 8280. (h) Braun, N. A.; Ciufolini, M. A.; Peters, K.; Peters, E.-M. Tetrahedron Lett. 1998, 39, 4667. (i) Snider, B. B.; Lin, H.; Foxman, B. M. J. Org. Chem. 1998, 63, 6442. (j) Kropf, J. E.; Weinreb, S. M. Abstracts of Papers, 222nd National Meeting of the American Chemical Society, Chicago, IL, August 26-30, 2001; American Chemical Society: Washington, DC, 2001; ORGN-373. (k) Bonjoch, J.; Diaba, F.; Puigbo, E.; Sole, D.; Segarra, V.; Santamaria, L.; Beleta, J.; Ryder, H.; Palacios, J.-M. Biorg. Med. Chem. 1999, 7, 2891. (l) Brummond, K. M.; Lu, J. Org. Lett. 2001, 3, 1347. (m) Bonjoch, J.; Diaba, F.; Puigbo, E.; Sole, D. Tetrahedron Lett. 2003, 44, 8387 (n) Panchaud, P.; Ollivier, C.; Renaud, P.; Zigmantas, S. J. Org. Chem. 2004, 69, 2755.
9. For approaches to FR901483 and its analogues, see: (f) Quirante, J.; Escolano, C.; Massot, M.; Bonjoch, J. Tetrahedron 1997, 53, 1391. (g) Yamazaki, N.; Suzuki, H.; Kibayashi, C. J. Org. Chem. 1997, 62, 8280. (h) Braun, N. A.; Ciufolini, M. A.; Peters, K.; Peters, E.-M. Tetrahedron Lett. 1998, 39, 4667. (i) Snider, B. B.; Lin, H.; Foxman, B. M. J. Org. Chem. 1998, 63, 6442. (j) Kropf, J. E.; Weinreb, S. M. Abstracts of Papers, 222nd National Meeting of the American Chemical Society, Chicago, IL, August 26-30, 2001; American Chemical Society: Washington, DC, 2001; ORGN-373. (k) Bonjoch, J.; Diaba, F.; Puigbo, E.; Sole, D.; Segarra, V.; Santamaria, L.; Beleta, J.; Ryder, H.; Palacios, J.-M. Biorg. Med. Chem. 1999, 7, 2891. (l) Brummond, K. M.; Lu, J. Org. Lett. 2001, 3, 1347. (m) Bonjoch, J.; Diaba, F.; Puigbo, E.; Sole, D. Tetrahedron Lett. 2003, 44, 8387 (n) Panchaud, P.; Ollivier, C.; Renaud, P.; Zigmantas, S. J. Org. Chem. 2004, 69, 2755.
10. For approaches to FR901483 and its analogues, see: (f) Quirante, J.; Escolano, C.; Massot, M.; Bonjoch, J. Tetrahedron 1997, 53, 1391. (g) Yamazaki, N.; Suzuki, H.; Kibayashi, C. J. Org. Chem. 1997, 62, 8280. (h) Braun, N. A.; Ciufolini, M. A.; Peters, K.; Peters, E.-M. Tetrahedron Lett. 1998, 39, 4667. (i) Snider, B. B.; Lin, H.; Foxman, B. M. J. Org. Chem. 1998, 63, 6442. (j) Kropf, J. E.; Weinreb, S. M. Abstracts of Papers, 222nd National Meeting of the American Chemical Society, Chicago, IL, August 26-30, 2001; American Chemical Society: Washington, DC, 2001; ORGN-373. (k) Bonjoch, J.; Diaba, F.; Puigbo, E.; Sole, D.; Segarra, V.; Santamaria, L.; Beleta, J.; Ryder, H.; Palacios, J.-M. Biorg. Med. Chem. 1999, 7, 2891. (l) Brummond, K. M.; Lu, J. Org. Lett. 2001, 3, 1347. (m) Bonjoch, J.; Diaba, F.; Puigbo, E.; Sole, D. Tetrahedron Lett. 2003, 44, 8387 (n) Panchaud, P.; Ollivier, C.; Renaud, P.; Zigmantas, S. J. Org. Chem. 2004, 69, 2755.
11. For approaches to FR901483 and its analogues, see: (f) Quirante, J.; Escolano, C.; Massot, M.; Bonjoch, J. Tetrahedron 1997, 53, 1391. (g) Yamazaki, N.; Suzuki, H.; Kibayashi, C. J. Org. Chem. 1997, 62, 8280. (h) Braun, N. A.; Ciufolini, M. A.; Peters, K.; Peters, E.-M. Tetrahedron Lett. 1998, 39, 4667. (i) Snider, B. B.; Lin, H.; Foxman, B. M. J. Org. Chem. 1998, 63, 6442. (j) Kropf, J. E.; Weinreb, S. M. Abstracts of Papers, 222nd National Meeting of the American Chemical Society, Chicago, IL, August 26-30, 2001; American Chemical Society: Washington, DC, 2001; ORGN-373. (k) Bonjoch, J.; Diaba, F.; Puigbo, E.; Sole, D.; Segarra, V.; Santamaria, L.; Beleta, J.; Ryder, H.; Palacios, J.-M. Biorg. Med. Chem. 1999, 7, 2891. (l) Brummond, K. M.; Lu, J. Org. Lett. 2001, 3, 1347. (m) Bonjoch, J.; Diaba, F.; Puigbo, E.; Sole, D. Tetrahedron Lett. 2003, 44, 8387 (n) Panchaud, P.; Ollivier, C.; Renaud, P.; Zigmantas, S. J. Org. Chem. 2004, 69, 2755.
12. For approaches to FR901483 and its analogues, see: (f) Quirante, J.; Escolano, C.; Massot, M.; Bonjoch, J. Tetrahedron 1997, 53, 1391. (g) Yamazaki, N.; Suzuki, H.; Kibayashi, C. J. Org. Chem. 1997, 62, 8280. (h) Braun, N. A.; Ciufolini, M. A.; Peters, K.; Peters, E.-M. Tetrahedron Lett. 1998, 39, 4667. (i) Snider, B. B.; Lin, H.; Foxman, B. M. J. Org. Chem. 1998, 63, 6442. (j) Kropf, J. E.; Weinreb, S. M. Abstracts of Papers, 222nd National Meeting of the American Chemical Society, Chicago, IL, August 26-30, 2001; American Chemical Society: Washington, DC, 2001; ORGN-373. (k) Bonjoch, J.; Diaba, F.; Puigbo, E.; Sole, D.; Segarra, V.; Santamaria, L.; Beleta, J.; Ryder, H.; Palacios, J.-M. Biorg. Med. Chem. 1999, 7, 2891. (l) Brummond, K. M.; Lu, J. Org. Lett. 2001, 3, 1347. (m) Bonjoch, J.; Diaba, F.; Puigbo, E.; Sole, D. Tetrahedron Lett. 2003, 44, 8387 (n) Panchaud, P.; Ollivier, C.; Renaud, P.; Zigmantas, S. J. Org. Chem. 2004, 69, 2755.
13. For approaches to FR901483 and its analogues, see: (f) Quirante, J.; Escolano, C.; Massot, M.; Bonjoch, J. Tetrahedron 1997, 53, 1391. (g) Yamazaki, N.; Suzuki, H.; Kibayashi, C. J. Org. Chem. 1997, 62, 8280. (h) Braun, N. A.; Ciufolini, M. A.; Peters, K.; Peters, E.-M. Tetrahedron Lett. 1998, 39, 4667. (i) Snider, B. B.; Lin, H.; Foxman, B. M. J. Org. Chem. 1998, 63, 6442. (j) Kropf, J. E.; Weinreb, S. M. Abstracts of Papers, 222nd National Meeting of the American Chemical Society, Chicago, IL, August 26-30, 2001; American Chemical Society: Washington, DC, 2001; ORGN-373. (k) Bonjoch, J.; Diaba, F.; Puigbo, E.; Sole, D.; Segarra, V.; Santamaria, L.; Beleta, J.; Ryder, H.; Palacios, J.-M. Biorg. Med. Chem. 1999, 7, 2891. (l) Brummond, K. M.; Lu, J. Org. Lett. 2001, 3, 1347. (m) Bonjoch, J.; Diaba, F.; Puigbo, E.; Sole, D. Tetrahedron Lett. 2003, 44, 8387 (n) Panchaud, P.; Ollivier, C.; Renaud, P.; Zigmantas, S. J. Org. Chem. 2004, 69, 2755.
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