Total synthesis of (-)-hemiasterlin, a structurally novel tripeptide that exhibits potent cytotoxic activity

Tetrahedron Letters

Volumn 38, Issue 3, 1997, Pages 317-320

  Andersen, Raymond J ^a   Coleman, John E ^a   Piers, Edward ^a   Wallace, Debra J ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; HEMIASTERLIN; TRIPEPTIDE; UNCLASSIFIED DRUG;

ARTICLE; BREAST CANCER; CELL CULTURE; CELL LINE; CONTROLLED STUDY; CYTOTOXICITY; DRUG SYNTHESIS; ENANTIOMER; HUMAN; HUMAN CELL; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SPONGE; TUMOR CELL;

EID: 0031032858     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02335-0     Document Type: Article

References (20)

1. Crews, P.; Farias, J. J.; Emrich, R.; Keifer, P. A. J. Org. Chem. 1994, 59, 2932.
2. Talpir, R.; Benayahu, Y.; Kashman, Y.; Pannell, L.; Schleyer, M. Tetrahedron Lett. 1994, 35, 4453.
3. Coleman, J. E.; de Silva, E. D.; Kong, F.; Andersen, R. J.; Allen, T. M. Tetrahedron 1995, 51, 10653.
4. Coleman, J. E.; Patrick, B. O.; Andersen, R. J.; Rettig, S. J. Acta Cryst. 1996, C52, 1525.
5. Andersen, H. J.; Coleman, J. E.; Andersen, R. J.; Roberge, M. Cancer Chemother. Pharmacol. In press.
6. Lassota, P. Personal communication.
7. The advisability of confirming the (apparent) biological activity of naturally occurring peptides by producing and testing the corresponding synthetic material was very recently underscored: Pettit, G. R.; Taylor, S. R. J. Org. Chem. 1996, 61, 2322.
8. All new compounds reported herein displayed spectra in accord with assigned structures and gave satisfactory elemental (C, H) analyses and/or molecular mass determinations (high-resolution mass spectrometry).
9. Griffith, W. P.; Ley, S. V. Aldrichim. Acta 1990, 23, 13.
10. 2OMe]Cl and t-BuOK in THF at room temperature.
11. Bal, B. S.; Childers, W. E., Jr.; Pinnick, H. W. Tetrahedron 1981, 37, 2091.
12. Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127.
13. Evans, D. A.; Britton, T. C.; Ellman, J. A.; Dorow, R. L. J. Am. Chem. Soc. 1990, 112, 4011.
14. Evans, D. A.; Evrard, D. A.; Rychnovsky, S. D.; Früh, T.; Whittingham, W. G.; DeVries, K. M. Tetrahedron Lett. 1992, 33, 1189.
15. Evans, D. A.; Britton, T. C.; Ellman, J. A. Tetrahedron Lett. 1987, 28, 6141.
16. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815.
17. Fehrentz, J.-A.; Castro, B. Synthesis 1983, 676.
18. Frérot, E; Coste, J.; Pantaloni, A.; Dufour, M.-N.; Jouin, P. Tetrahedron 1991, 47, 259.
19. 20 gave a similar yield of the corresponding dipeptide derivative. Attempts to improve the efficiency of the formation of 23 (or a synthetically equivalent intermediate) are in progress. Equation represented.
20. Frérot, E; Coste, J.; Poncet, J.; Jouin, P.; Castro, B. Tetrahedron Lett. 1992, 33, 2815.