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Volumn 118, Issue 44, 1996, Pages 10752-10765

Toluene dioxygenase-mediated cis-dihydroxylation of aromatics in enantioselective synthesis. Asymmetric total syntheses of pancratistatin and 7-deoxypancratistatin, promising antitumor agents

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; PANCRATISTATIN; UNCLASSIFIED DRUG;

EID: 0029798274     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja960596j     Document Type: Article
Times cited : (181)

References (144)
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    • The word pancratistatin should more appropriately be spelled pancratistatinum in correct "chemical" Latin. It implies an "all-powerful breaker or stopper" of some activity, in this case cell division. The derivation is of some interest here. The name of the plant translates literally as "all-powerful from the shore of a lake" and is a Latin rendition of a Greek word pankration, which means "victory by any and all means", It refers to an ancient wrestling contest which was frequently fought to the death or unconditional surrender of one of the opponents. Barred from this match was only the use of biting or gouging - all else was allowed. The root of the word pankration in Greek implies power or strength (kratos) and in Latin hurdles or obstacles. We thank Dr. Thomas MacAdoo (Virginia Tech) for this interesting elucidation.
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    • Available from Eastman Fine Chemicals, Rochester, NY, and Genencor International, Inc., South San Francisco, CA
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    • 18c equation presented
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    • (a) We thank Dr. Jonathan Clayden, University of Manchester, for bringing this possibility to our attention,
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    • A sample of 4 was kindly provided by Prof. G. R. Pettit of Arizona State University.
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    • Methyl carbamate was prepared according to the procedure for the corresponding ethyl carbamate: Lwowski, W.; Maricich, T. J.; Mattingly, T. W., Jr. J. Am. Chem. Soc. 1963, 85, 1200. For the aziridination, compare: (a) Lwowski, W.; Maricich, T. J. J. Am. Chem. Soc. 1965, 87, 3630. (b) Fioravanti, S.; Loreto, M. A.; Pellacani, L.; Tardella, P. A, Tetrahedron Lett. 1993, 34, 4353.
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    • Methyl carbamate was prepared according to the procedure for the corresponding ethyl carbamate: Lwowski, W.; Maricich, T. J.; Mattingly, T. W., Jr. J. Am. Chem. Soc. 1963, 85, 1200. For the aziridination, compare: (a) Lwowski, W.; Maricich, T. J. J. Am. Chem. Soc. 1965, 87, 3630. (b) Fioravanti, S.; Loreto, M. A.; Pellacani, L.; Tardella, P. A, Tetrahedron Lett. 1993, 34, 4353.
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