Synthesis of dolastatin G and nordolastatin G, cytotoxic 35-membered cyclodepsipeptides of marine origin

Tetrahedron Letters

Volumn 37, Issue 40, 1996, Pages 7299-7302

  Mutou, Tsuyoshi ^a   Kondo, Takashi ^a   Shibata, Takunobu ^a   Ojika, Makoto ^a   Kigoshi, Hideo ^a   Yamada, Kiyoyuki ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DOLASTATIN G; NORDOLASTATIN G; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 0030607236     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01653-X     Document Type: Article

References (14)

1. 1. Mutou, T.; Kondo, T.; Ojika, M.; Yamada, Y. J. Org. Chem., in press.
2. 1H NMR, and mass) and analytical (elemental analyses or high-resolution mass spectral analyses) data were obtained for all new compounds.
3. 3. Yamada, S.; Kasai, Y.; Shioiri, T. Tetrahedron Lett. 1973, 1595-1598.
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7. 7. Kock, P.; Nakatani, Y.; Luu, B.; Ourisson, G. Bull. Soc. Chim. Fr. 1983, 189-194.
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10. 10. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.
11. 1] One of referees pointed out the possibility that the racemization of the C-terminal L-proline residue may occur during the preparation of 3. This possibility is excluded by the fact that the acid hydrolysis of 3 gave only L-proline.
12. 2, 23 °C), afforded not the desired macrocyclic compound, nordolastatin G (2), but a complex mixture containing a compound resulting from decarboxylation of the β-keto acid portion.
13. 13. For the use of montmorillonite K 10 in the preparation of a dimethyl acetal group, see: Tayler, E. C.; Chiang, C. C. Synthesis 1977, 467.
14. 14. Tung, R. D.; Rich, D. H. J. Am. Chem. Soc. 1985, 107, 4342-4343. (equation presented)