Total synthesis of (-)-dictyostatin: Confirmation of relative and absolute configurations

Angewandte Chemie - International Edition

Volumn 43, Issue 35, 2004, Pages 4634-4637

  Shin, Youseung ^a   Fournier, Jean Hugues ^a   Fukui, Yoshikazu ^a   Brückner, Arndt M ^a   Curran, Dennis P ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

Antitumor agents; Conformation analysis; Macrocycles; Natural products; Total synthesis

Indexed keywords

CONFORMATIONS; SYNTHESIS (CHEMICAL); TUMORS;

ANTICANCER AGENTS; DICTYOSTATIN; ENANTIOMERS;

STEREOCHEMISTRY;

ANTINEOPLASTIC AGENT; DICTYOSTATIN; DISCODERMOLIDE; MACROLIDE; UNCLASSIFIED DRUG;

ARTICLE; DRUG CONFORMATION; DRUG DESIGN; DRUG SYNTHESIS; HYBRID; ISOMER; ISOMERIZATION; MACROLACTONIZATION; NONHUMAN; SPONGE (PORIFERA); STEREOCHEMISTRY; STRUCTURE ANALYSIS;

MACROLIDES; MOLECULAR CONFORMATION;

EID: 5344247972     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460593     Document Type: Article

References (33)

1. a) G. R. Pettit, Z. A. Cichacz, F. Gao, M. R. Boyd, J. M. Schmidt, J. Chem. Soc. Chem. Commun. 1994, 1111-1112;
2. b) G. R. Pettit, Z. A. Cichacz, Isolation and structure of dictyostatin, WO 5430053, 1995 [Chem. Abstr. 1995,733500].
3. a) A. E. Wright, J. L. Cummins, S. A. Pomponi, R. E. Longley, R. A. Isbrucker, Dictyostatin compounds for stabilization of microtubules, WO 0162239, 2001 [Chem. Abstr. 2001, 635882];
4. b) R. A. Isbrucker, J. Cummins, S. A. Pomponi, R. E. Longley, A. E. Wright, Biochem. Pharmacol. 2003, 66, 75-82.
5. a) M. Kalesse, ChemBioChem 2000, 1, 171-175;
6. b) D. C. Myles, Annu. Rep. Med. Chem. 2002, 37, 125-132;
7. c) I. Paterson, G. J. Florence, Eur. J. Org. Chem. 2003, 2193-2208;
8. d) S. J. Mickel, G. H. Sedelmeier, D. Niederer, R. Daeffler, A. Osmani, K. Schreiner, M. Seeger-Weibel, B. Berod, K. Schaer, R. Gamboni, Org. Process Res. Dev. 2004, 8, 92-100, and succeeding papers in that issue.
9. Y. Shin, N. Choy, R. Balachandran, C. Madiraju, B. W. Day, D. P. Curran, Org. Lett. 2002, 4, 4443-4446.
10. a) Y. Shin, unpublished results; syntheses of isomers of dictyostatin will be described in a subsequent full paper;
11. b) D. P. Curran, Y. Shin, N. Choy, B. W. Day, R. Balachandran, C. Madiraju, T. Turner, WO 022552, 2004 [Chem. Abstr. 2004, 220327].
12. I. Paterson, R. Britton, O. Delgado, A. E. Wright, Chem. Commun. 2004, 632-633.
13. The numbering system of discodermolide is imposed on dictyostatin in this paper to facilitate comparisons.
14. See preceding Communication in this issue: I. Paterson, R. Britton, O. Delgado, A. Meyer, K. G. Poullennec, Angew. Chem. 2004, 116, 4729; Angew. Chem. Int. Ed., 2004, 43, 4629.
15. See preceding Communication in this issue: I. Paterson, R. Britton, O. Delgado, A. Meyer, K. G. Poullennec, Angew. Chem. 2004, 116, 4729; Angew. Chem. Int. Ed., 2004, 43, 4629.
16. a) A. B. Smith III, T. J. Beauchamp, M. J. LaMarche, M. D. Kaufman, Y. P. Qiu, H. Arimoto, D. R. Jones, K. Kobayashi, J. Am. Chem. Soc. 2000, 122, 8654-8664;
17. b) Weinreb amide 8 was made in five steps from (2S)-3-hydroxy-2- methylpropionic acid methyl ester (Roche ester) in 39% yield. Roche ester was purchased from Aldrich or Mitsubishi-Rayon.
18. a) N. Choy, Y. Shin, P. Q. Nguyen, D. P. Curran, R. Balachandran, C. Madiraju, B. W. Day, J. Med. Chem. 2003, 46, 2846-2860;
19. b) J. M. Minguez, S.-Y. Kim, K. A. Giuliano, R. Balachandran, C. Madiraju, B. W. Day, D. P. Curran, Bioorg. Med. Chem. 2003, 11, 3335-3354.
20. J. A. Marshall, M. J. Bourbeau, Org. Lett. 2003, 5, 3197-3199.
21. a) R. D. Walkup, R. R. Kane, P. D. Boatman Jr, R. T. Cunningham, Tetrahedron Lett. 1990, 31, 7587-7609;
22. b) R. D. Walkup, J. D. Kahl, R. R. Kane, J. Org. Chem. 1998, 63, 9113-9116;
23. c) alcohol 9 was made in five steps from Roche ester in 47% yield.
24. A. Myers, B. Y. Yang, H. Chen, L. McKinstry, D. J. Kopecky, J. Gleason, J. Am. Chem. Soc. 1997, 119, 6496-6511.
25. The enantiomer of the methyl ester of 6 is known: a) P. Phukan, S. Sasmal, M. E. Maier, Eur. J. Org. Chem. 2003, 1733-1740; b) M. B. Andrus, A. B. Argade, Tetrahedron Lett. 1996, 37, 5049-5052; c) ester 11 was made in six steps from 1,3-propanediol in 35 % yield.
26. The enantiomer of the methyl ester of 6 is known: a) P. Phukan, S. Sasmal, M. E. Maier, Eur. J. Org. Chem. 2003, 1733-1740; b) M. B. Andrus, A. B. Argade, Tetrahedron Lett. 1996, 37, 5049-5052; c) ester 11 was made in six steps from 1,3-propanediol in 35 % yield.
27. The enantiomer of the methyl ester of 6 is known: a) P. Phukan, S. Sasmal, M. E. Maier, Eur. J. Org. Chem. 2003, 1733-1740; b) M. B. Andrus, A. B. Argade, Tetrahedron Lett. 1996, 37, 5049-5052; c) ester 11 was made in six steps from 1,3-propanediol in 35 % yield.
28. K. Matsumura, S. Hashiguchi, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1997, 119, 8738-8739.
29. The nonselective reduction was expressly used to make both isomers because the configuration at this center was at issue.
30. I. Paterson, G. J. Florence, K. Gerlach, J. P. Scott, N. Sereinig, J. Am. Chem. Soc. 2001, 123, 9535-9544.
31. W. C. Still, C. Gennari, Tetrahedron Lett. 1983, 24, 4405-4408.
32. J. Inanaga, H. Kuniko, S. Hiroko, T. Katsuki, M. Yamaguchi, Bull. Chem. Soc. Jpn. 1979, 52, 1989-1994.
33. Dr. Robert Britton, Cambridge University, kindly recorded 500 MHz NMR spectra of our sample and a natural sample provided by Dr. Amy Wright, Harbor Branch Ocenanographic Institute. These spectra are in the Supporting Information.