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A Short and Efficient Enantiomeric Synthesis of Antitumor Fused Tetrahydrofurans

AuthorsPinacho Crisóstomo, Fernando R. ; Padrón, José M.; Martín, Tomás ; Villar, Jesús; Martín, Víctor S.
KeywordsAntitumor agents
Cyclic ethers
Asymmetric synthesis
Structure–activity relationships
Issue DateApr-2006
CitationEuropean Journal of Organic Chemistry 8: 1910-1916 (2006)
Abstractshort and efficient enantiomeric synthesis of fused tetrahydrofuran derivatives is reported. The methodology is based on a regio- and stereoselective double exo-cyclization of enantiomeric bis-epoxy-diols. The six stereocenters of the bis-epoxy diols were introduced by the application of Katsuki–Sharpless asymmetric epoxidation and Sharpless asymmetric dihydroxylation reactions. In vitro cytotoxicities on HL60 human promyelocytic leukemia cells were determined for the bicyclic products. Active products showed exceptionally steep dose–response curves and DNA laddering.
Description7 páginas, 3 figuras, 1 tabla, 4 esquemas.
Publisher version (URL)http://dx.doi.org/10.1002/ejoc.200500842
Appears in Collections:(IPNA) Artículos
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