First total synthesis of dragmacidin A via indolylglycines

Organic Letters

Volumn 2, Issue 19, 2000, Pages 3027-3029

  Kawasaki, Tomomi ^a   Enoki, Hidetaka ^a   Matsumura, Ken ^a   Ohyama, Miho ^a   Inagawa, Masato ^a   Sakamoto, Masanori ^a  

^a MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DRAGMACIDIN A; DRUG DERIVATIVE; GLYCINE; INDOLE DERIVATIVE; PIPERAZINE DERIVATIVE;

ANIMAL; ARTICLE; CHEMISTRY; SPONGE (PORIFERA); SYNTHESIS;

ANIMALS; GLYCINE; INDOLES; PIPERAZINES; PORIFERA;

EID: 0034699305     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006394g     Document Type: Article

References (24)

1. Dragmacidin (1a): Kohmoto, S.; Kashmann, Y.; McConnell, O. J.; Rinehart, K. L. Jr.; Wright, A.; Koehn, F. J. Org. Chem. 1988, 53, 3116-3118.
2. Dragmacidin A (1b) and dragmacidin B (1c): Morris S. A.; Andersen, R. J. Tetrahedron 1990, 46, 715-720.
3. Dragmacidin C (1d): Fahy, E.; Potts, B. C. M.; Faulkner, D. J.; Smith, K. J. Nat. Prod. 1991, 54, 564-569.
4. Dragmacidin D (1e): Wright, A. E.; Pomponi, S. A.; Cross, S. S.; McCarthy. P. J. Org. Chem. 1992, 57, 4772-4775.
5. Dragmacidin E (1f): 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.
6. Dragmacidin F (1g): (a) Cutignano, A.; Bifulco, G.; Bruno, I.; Casapullo, A.; Gomez-Paloma, L.; Riccio, R. Tetrahedron 2000, 56, 3743-3748.
7. (b) Write, A. E.; Pomponi, S. A.; Jacobs, R. S. U. S. Pat. US 3655, 1999.
8. Jiang, B.; Smallheer, J. M.; Amaral-Ly, A.; Wuonola, M. A. J. Org. Chem. 1994, 59, 6823-6827.
9. Whitlock, C. R.; Cava, M. P. Tetrahedron Lett. 1994, 35, 371-374.
10. (a) Droste, H.; Wieland, T. Liebigs Ann. Chem. 1987, 901-910.
11. (b) O'Donnell, M. J.; Bennett, W. D. Tetrahedron 1988, 44, 5389-5401.
12. (c) Bergman, J.; Bergman, S.; Lindströn, J.-O. Tetrahedron Lett. 1989, 30, 5337-5340.
13. (d) Heaney, H.; Papageorgiou, G.; Wilkins, R. F. Tetrahedron 1997, 53, 2941-2958.
14. (e) Clark, B. P.; Harris, J. R. Synth. Commun. 1997, 27, 4223-4234.
15. (f) Recently N-tosyl indolylglycines were prepared by the copper(I)-catalyzed addition of N-tosylimino ester to indoles with electron-withdrawing substituents: Johannsen. M. Chem. Commun. 1999, 2233-2234.
16. Kawasaki, T.; Nonaka, Y.; Matsumura, K.; Monai, M.; Sakamoto, M. Synth. Commun. 1999, 29, 3251-3261.
17. Arnarp, J.; Lönngren, J. Acta Chem. Scand. B 1978, 32, 465-467.
18. DTBMP, 2,6-di-tert-butyl-4-methylpyridine; PFP, pentafluorophenol; BOP, benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate.
19. Greene, T. W.; Wuts, P. G. Protective Groups in Organic Synthesis, 3rd ed.; John Wiley & Sons: New York, 1999; pp 518-525.
20. In some cases, deamination was observed as an undesired reaction.
21. We also attempted to use benzyl ester; however, the hydrogenatic deprotection of the benzyl group led to debromination.
22. The stereochemistry was confirmed by transformation to 1b and its NOE experiments.
23. King, R. R. Can. J. Chem. 1997, 75, 1172-1173.
24. Treatment at temperatures higher than 10°C resulted in epimerization to give a mixture of trans-and cis-isomers of 2.