Stereoselective synthesis and biological evaluation of anisomycin and 2- substituted analogues

Synthesis

Volumn , Issue SPEC. ISS., 1999, Pages 1473-1490

  Schwardt, Oliver ^a   Veith, Ulrich ^a   Gaspard, Christiane ^b   Jäger, Volker ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

^b CNRS   (France)

Author keywords

1,4 amino alcohol cyclization; Anisomycin; Cytotoxicity; Diastereoselective 1,2 addition; Dihydroxypyrrolidine; Threose imine

Indexed keywords

1 BENZYL 3 (BENZYLOXY) 4 HYDROXY 2 (4 METHOXYBENZYL)PYRROLIDINE; 1,2 DIBENZYL 3 (BENZYLOXY) 4 HYDROXYPYRROLIDINE; 3 ACETOXY 2 BENZYL 4 HYDROXYPYRROLIDINE HYDROCHLORIDE(DEMETHOXYANISOMYCIN HYDROCHLORIDE); 3 BENZOYLOXY 4 HYDROXY 2 (4 METHOXYBENZYL)PYRROLIDINE HYDROCHLORIDE; 3,4 DIACETYL 3,4 DIHYDROXY 2 (4 METHOXYBENZYL)PYRROLIDINE HYDROCHLORIDE(4 O ACETYLANISOMYCIN HYDROCHLORIDE; 3,4 DIHYDROXY 2 (4 METHOXYBENZYL)PYRROLIDINE HYDROBROMIDE( DEACETYLANISOMYCIN HYDROBROMIDE); ANISOMYCIN; DEACETYLANISOMYCIN; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CYTOTOXICITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; STEREOCHEMISTRY;

EID: 0032806922     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3661     Document Type: Article

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3. b) Part of these results have been presented: Schwardt, O.; Veith, U.; Gaspard, C.; Jäger, V. 2nd Lausanne Conf. on Bioorg. Chem., Lausanne, Switzerland, 6.-7.3.1997, Abstr. P 26;. Schwardt, O.; Veith, U.; Gaspard, C.; Jäger, V.., Orchem 98, Bad Nauheim, Germany, 10.-12.9.1998, Abstr. P 151.
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86. For the influence of an α-benzyloxy group on the addition to ketones and for kinetic investigation concerning Cram's rule ("Cram-chelate") see: Eliel, E. L.; Frye, S. V.; Hortelano, E. R.; Chen, X.; Bai, X. Pure Appl. Chem. 1991, 63, 1591. Chen, X.; Hortelano, E. R.; Eliel, E. L.; Frye, S. V. J. Am. Chem. Soc. 1990, 112, 6130. Chen, X.; Hortelano, E. R.; Eliel, E. L.; Frye, S. V. J. Am. Chem. Soc. 1992, 114, 1778.
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