Dolastatins. 26. Synthesis and stereochemistry of dolastatin 11

Journal of the American Chemical Society

Volumn 119, Issue 9, 1997, Pages 2111-2113

  Bates, Robert B ^a   Brusoe, Kennard G ^a   Burns, Jennifer J ^a   Caldera, Sriyani ^a   Cui, Wei ^a   Gangwar, Sanjeev ^a   Gramme, Michelle R ^a   McClure, Kelly J ^a   Rouen, Gregory P ^a   Schadow, Heiko ^a   Stessman, Chad C ^a   Taylor, Stuart R ^a   Vu, Vicky H ^a   Yarick, Gayle V ^a   Zhang, Jianxing ^a   Pettit, George R ^b   Bontems, Roger ^b  

^a University of Arizona   (United States)

^b UNIVERSITY OF ARIZONA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DOLASTATIN; DOLASTATIN 11; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 16944362479     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja963857y     Document Type: Article

References (15)

1. (a) For the previous contribution in this series refer to Antineoplastic Agents. 383: G. P. Kalemkerian, X. Ou, S. K. Madan, and G. R. Pettit, manuscript in preparation.
2. (b) Pettit, G. R.; Kamano, Y.; Kizu, H.; Dufresne, C.; Herald, C. L.; Bontems, R.; Schmidt, J. M.; Boettner, F. E.; Nieman, R. A. Heterocycles 1989, 28, 553.
3. Carter, D. C.; Moore, R. E.; Mynderse, J. S.; Niemczura, W. P.; Todd, J. S. J. Org. Chem. 1984, 49, 236.
4. Mynderse, J. S.; Hunt, A. H.; Moore, R. E. J. Nat. Prod. 1988, 51, 1299.
5. Bates, R. B.; Gangwar, S. Tetrahedron: Asymmetry 1993, 4, 69.
6. Hamada, Y.; Kondo, Y.; Shibata, M.; Shioiri, T. J. Am. Chem. Soc. 1989, 111, 669.
7. Davies, S. G.; Ichihara, O.; Walters, I. A. S. Synlett 1994, 117.
8. Jefford, C. W.; McNulty, J. Helv. Chim. Acta 1994, 77, 2142.
9. Pfeffer, P. E.; Silbert, L. S. Liebig's Ann. Chem. 1970, 55, 262.
10. 5 to make ethyl lithioacetate.
11. Scheibler, H.; Wheeler, A. S. Ber. Dtsch. Chem. Ges. 1911, 44, 2684.
12. Dourtoglou, V.; Gross, B.; Lambropoulou, V.; Zioudrou, C. Synthesis 1984, 572.
13. Tung, R. D.; Rich, D. H. J. Am. Chem. Soc. 1985, 107, 4342.
14. Dolastatin 11 (1) was recently placed in preclinical development by the National Cancer Institute (Pettit, G. R. J. Nat. Prod. 1996, 59, 812).
15. Erlich, A.; Rothemund, S.; Brudel, M.; Beyermann, M.; Carpino, L. A.; Bienert, M. Tetrahedron Lett. 1993, 34, 4781.