The Structure and Synthesis of Dolastatin 3la

Journal of the American Chemical Society

Volumn 109, Issue 24, 1987, Pages 7581-7582

  Pettit, George R ^a   Kamano, Yoshiaki ^a   Holzapfel, Cedric W ^a   Van Zyl, Wynand J ^a   Tuinman, Albert A ^a   Herald, Cherry L ^a   Baczynskyj, Lubomir ^a   Schmidt, Jean M ^a  

^a ARIZONA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DOLASTATIN 3;

DRUG ANALYSIS; NONHUMAN; PRELIMINARY COMMUNICATION; THEORETICAL STUDY;

EID: 0023627754     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00258a081     Document Type: Article

References (12)

1. (a) Antineoplastic agents series contribution 150: for part 149 consult: Daniel, L. W.; Parker, J.; Etkins, L. A.; Small, G. W.; Pettit, G. R. J. Biol. Chem., submitted for publication. Rand Afrikaans University, Johannesburg, Republic of South Africa. Present address: University of Tennessee. Knoxville. TN 37996. (d) The Upjohn Co., Kalamazoo, Ml 49001.
2. Pettit, G. R.; Kamano, Y.; Brown, P.; Gust, D.: Inoue, M.; Herald, C. L. J. Am. Chem. Soc. 1982, 104, 905–907.
3. (a) Pettit, G. R.; Holzapfel, C. W. J. Org. Chem. 1986, 51, 4580–4585. Pettit, G. R.; Nelson, P. S.; Holzapfel, C. W. J. Org. Chem. 1985, 50, 2654–2659. Pettit, G. R.; Holzapfel, C. W. J. Org. Chem. 1986, 51, 4586–4590.
4. (a) Eckart, K.; Schmidt, U.; Shwartz, H. Liebigs Ann. Chem. 1986, 1940. Schmidt, U.; Utz, R. Angew. Chem. 1984, 96, 725–726. Hamada, Y.; Kohda, K.; Shioiri, T. Tetrahedron Lett. 1984, 25, 5303–5306. (d) Schmidt, U.; Weller, D. Tetrahedron Lett. 1986, 27, 3495–3496. (e) Schmidt, U.; Utz, R.; Lieberknecht, A.; Griesser, H.; Potzolli, B.; Bahr, J.; Wagner, K.; Fischer, P. Synthesis 1987, 236–241.
5. Bernier, J. L.; Houssin, R.; Henichart, J. P. Tetrahedron 1986, 42, 2695–2702.
6. Over this period structures proposed in other laboratories for patel-lamides AC, another group of antineoplastic cyclic peptides (from a marine tunicate) containing thiazole amino acid units, were also undergoing revision and reassignment based on total syntheses, cf.: Schmidt, U.; Griesser, H. Tetrahedron Lett. 1986, 27, 163–166. Hamada, Y.; Shibata, M.; Shioiri, T. Tetrahedron Lett. 1985, 26, 6501–6504. Hamada, Y.; Shibata, M.; Shioiri, T. Tetrahedron Lett. 1985, 26, 5159–5162. Hamada, Y.; Shibata, M.; Shioiri, T. Tetrahedron Lett. 1985, 26, 5155–5158. Hamada, Y.; Kato, S.; Shioiri, T. Tetrahedron Lett. 1985, 26, 3223–3226. Kato, S.; Kondo, Y.; Sugiura, T.; Hamada, Y.; Shioiri, T. Peptide Chemistry, Protein Research Foundation: Minoh-shi, Osaka 562, Japan, 1985; pp 67–72.
7. A useful conformational analysis of the 350-MHz spectrum [in (CD3)2SO] of cy£7o[Pro-Leu-Val-(gly)Thz-(gly)Thz] has been entered in ref
8. For leading references consult: Pettit, G. R. Synthetic Peptides; Elsevier: Amsterdam, The Netherlands, 1982, Vol. 6. Pettit, G. R. Synthetic Peptides; Elsevier: Amsterdam, The Netherlands, 1980; Vol. 5.
9. Schmidt, U.; Utz, R.; Lieberknecht, A.; Griesser, H.; Potzolli, B.; Bahr, J.; Wagner, K.; Fischer, P. Synthesis 1987, 233–236. Schmidt, U.; Gleich, P.; Griesser, H.; Utz, R. Synthesis 1986, 992–998. Kelly, R. C.; Gebhard, I.; Wicnienski, N. J. Org. Chem. 1986, 51, 4590–4594. Houssin, R.; Lohez, M.; Bernier, J. L.; Henichart, J. P. J. Org. Chem. 1985, 50, 2787–2788. Holzapfel, C. W.; Pettit, G. R. J. Org. Chem. 1985, 50, 2323–2327.
10. Schmidt, U,; Lieberknecht, A.; Griesser, H.; Utz, R.; Beuttler, T.; Bartkowiak, F. Synthesis 1986, 5, 361. Schmidt, U.; Gleich, P. Angew. Chem., Int. Ed. Engl. 1985, 24, 569–571.
11. Satisfactory mass and NMR (‘H and 13 spectral and elemental analyses were obtained for each of the synthetic products. The following HR SP-SIMS results were obtained for dolastatin 3. Anal. Calcd for C29H41-N806S2(M + H) 661.2591, found (natural) 661.2600 and found (synthetic) 661.2576.
12. Holzapfel, C. W.; Pettit, G. R.; Cragg, G. M. J. Nat. Prod. 1985, 48, 513.