Enantioselective Total Synthesis of Eurylene, 14-Deacetyl Eurylene, and Their 11-Epimers:  The Relation between Ionophoric Nature and Cytotoxicity

Enantioselective synthesis of eurylene, 14-deacetyl eurylene, and their 11-epimers was achieved. The characteristic structural feature of these compounds is two tetrahydrofuran (THF) rings substituted in different stereochemistry. The synthetic approach involves nonstereoselective THF ring formation...

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Bibliographic Details
Published in:Organic letters 2004-03, Vol.6 (6), p.961-964
Main Authors: Hioki, Hideaki, Yoshio, Suzuyo, Motosue, Masatoshi, Oshita, Yuka, Nakamura, Yukari, Mishima, Daisaku, Fukuyama, Yoshiyasu, Kodama, Mitsuaki, Ueda, Keisuke, Katsu, Takashi
Format: Article
Language:English
Subjects:
Eurycoma
Furans - chemical synthesis
Furans - chemistry
Furans - pharmacology
Furans - toxicity
Humans
Ionophores - chemistry
KB Cells
Molecular Structure
Plant Bark - chemistry
Potassium - chemistry
Triterpenes - chemical synthesis
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Summary:Enantioselective synthesis of eurylene, 14-deacetyl eurylene, and their 11-epimers was achieved. The characteristic structural feature of these compounds is two tetrahydrofuran (THF) rings substituted in different stereochemistry. The synthetic approach involves nonstereoselective THF ring formation to afford both segments from a common precursor. We also investigated their ionophoric nature and cytotoxicity. The complexation of these compounds with K+ might be related to their cytotoxic activity.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol036471i