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- W1971139947 abstract "Tetrahydrofurans and γ-Lactones, V[1,2]. — Optically Active δ-Hydroxy-γ-lactones from Cyclooctyne and Furan — Synthesis of (—)-(R,R)- and (+)-(S,S)-Muricatacin and Related Compounds The γ-lactone 1a, easily available from cyclooctyne and furan is converted to enantiomerically pure (—)-(R,R)- and (+)-(S,S)-muricatacin (2e). Compound 2e was isolated recently as a biologically active (R,R/S,S) mixture from the seeds of Annona muricata. Optically active compounds were obtained by chromatographic separation of the diastereomeric camphanoates (4R)-4a and (4S)-4b and subsequent highly diastereoselective reduction with L-Selectride≫ to give finally (4R,5R)- and (4S,5S)-2c. The necessary side chain was introduced via Wittig reaction of the aldehyde 3c. Absolute configuration of all new products were established by X-ray structural analysis of the δ-lactone 7a and by comparison of (–)-2f with its known dextrorotatory enantiomer as well. According to Mosher ester analysis of (—)-2c and (—)-2e the ee is ≥98%. The synthesis of rac-muricatacin is also described. The scope of this new approach to functionalized dodecane (di)acid derivatives 3a–3c with (4R,5R) and (4S,5S) configuration is discussed." @default.
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- W1971139947 date "1992-10-12" @default.
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- W1971139947 title "Tetrahydrofurane und γ-Lactone, V[1,2] Optisch aktive δ-Hydroxy-γ-lactone aus Cyclooctin und Furan — Synthese von (—)-(R,R)- und (+)-(S,S)-Muricatacin sowie verwandter Verbindungen" @default.
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- W1971139947 doi "https://doi.org/10.1002/jlac.1992199201176" @default.
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