The total synthesis of (+)-dragmacidin F

Journal of the American Chemical Society

Volumn 126, Issue 31, 2004, Pages 9552-9553

  Garg, Neil K ^a   Caspi, Daniel D ^a   Stoltz, Brian M ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

6 BROMOINDOLE; ALKALOID; ANTIVIRUS AGENT; DRAGMACIDIN F; IMIDAZOLE DERIVATIVE; INDOLE DERIVATIVE; LACTONE DERIVATIVE; PALLADIUM; PYRAZINE DERIVATIVE; PYRAZINONE DERIVATIVE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; ENANTIOMER; HALICORTEX; HERPES SIMPLEX VIRUS 1; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN IMMUNODEFICIENCY VIRUS 1; INFRARED SPECTROSCOPY; NEBER REARRANGEMENT; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; SPONGE (PORIFERA); STEREOSPECIFICITY; SUZUKI REACTION; ULTRAVIOLET SPECTROSCOPY;

ANIMALS; ANTI-HIV AGENTS; ANTIVIRAL AGENTS; INDOLE ALKALOIDS; PORIFERA; STEREOISOMERISM;

EID: 3543120754     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja046695b     Document Type: Article

References (30)

1. (a) Wright, A. E.; Pomponi, S. A.; Cross, S. S.; McCarthy, P. J. Org. Chem. 1992, 57, 4772-4775.
2. (b) Capon, R. J.; Rooney, F.; Murray, L. M.; Collins, E.; Sim, A. T. R.; Rostas, J. A. P.; Butler, M. S.; Carroll, A. R. J. Nat. Prod. 1998, 61, 660-662.
3. (c) Cutignano, A.; Bifulco, G.; Bruno, I.; Casapullo, A.; Gomez-Paloma, L.; Riccio, R. Tetrahedron 2000, 56, 3743-3748 and references therein.
4. For synthetic work aimed toward the piperazine-containing dragmacidins, see: (a) Jiang, B.; Smallheer, J. M.; Amaral-Ly, C.; Wuonola, M. A. J. Org. Chem. 1994, 59, 6823-6827.
5. (b) Whitlock, C. R.; Cava, M. P. Tetrahedron Lett. 1994, 35, 371-374.
6. (c) Kawasaki, T.; Enoki, H.; Matsumura, K.; Ohyama, M.; Inagawa, M.; Sakamoto, M. Org. Lett. 2000, 2, 3027-3029.
7. (d) Miyake, F. Y.; Yakushijin, K.; Horne, D. A. Org. Lett. 2000, 2, 3185-3187.
8. (e) Yang, C.-G.; Wang, J.; Tang, X.-X.; Jiang, B. Tetrahedron: Asymmetry 2002, 13, 383-394.
9. (f) Kawasaki, T.; Ohno, K.; Enoki, H.; Umemoto, Y.; Sakamoto, M. Tetrahedron Lett. 2002, 43, 4245-4248. For studies targeting dragmacidins D, E, or F,
10. see: (g) Jiang, B.; Gu, X.-H. Bioorg. Med. Chem. 2000, 8, 363-371.
11. (h) Jiang, B.; Gu, X.-H. Heterocycles 2000, 53, 1559-1568.
12. (i) Yang, C.-G.; Wang, J.; Jiang, B. Tetrahedron Lett. 2002, 43, 1063-1066.
13. (J) Miyake, F. Y.; Yakushijin, K.; Horne, D. A. Org. Lett. 2002, 4, 941-943.
14. (k) Yang, C.-G.; Liu, G.; Jiang, B. J. Org. Chem. 2002, 67, 9392-9396.
15. Garg, N. K.; Sarpong, R.; Stoltz, B. M. J. Am. Chem. Soc. 2002, 124, 13179-13184.
16. (a) Stoltz, B. M. Chem. Lett. 2004, 33, 362-367 and references therein.
17. (b) Trend, R. M.; Ramtohul, Y. K.; Ferreira, E. M.; Stoltz, B. M. Angew. Chem., Int. Ed. 2003, 42, 2892-2895.
18. (c) Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2003, 125, 9578-9579.
19. (a) Philippe, M.; Sepulchre, A. M.; Gero, S. D.; Loibner, H.; Streicher, W.; Stutz, P. J. Antibiot. 1982, 35, 1507-1512.
20. (b) Manthey, M. K.; González-Bello, C.; Abell, C. J. Chem. Soc., Perkin Trans. 1 1997, 5, 625-628.
21. Preliminary mechanistic studies suggest that a Pd-catalyzed π-allyl reduction is not operative.
22. (a) Under optimized conditions,7b intramolecular Heck cyclization of related 3-bromopyrrole derivative i resulted in competitive production of undesired product ii.10b
23. (b) Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989-7000
24. Gilow, H. M.; Hong, Y. H.; Millirons, P. L.; Snyder, R. C.; Casteel, W. J., Jr. J. Heterocycl. Chem. 1986, 23, 1475-1480.
25. (a) Neber, P. W.; Friedolsheim, A. Justus Liebigs Ann. Chem. 1926, 449, 109-134.
26. (b) Ooi, T.; Takahashi, M.; Doda, K.; Maruoka, K. J. Am. Chem. Soc. 2002, 124, 7640-7641.
27. (c) To the best of our knowledge, the Neber rearrangement has not previously been carried out successfully in the context of natural product total synthesis.
28. (a) Purified by reversed-phase chromatography using trifluoroacetic acid in the eluent.
29. (b) See Supporting Information for details.
30. Dragmacidin numbering convention, see ref 1.