142925-95-9Relevant academic research and scientific papers
Tetrahydrofurans and γ-Lactones, V. - Optically Active δ-Hydroxy-γ-lactones from Cyclooctyne and Furan - Synthesis of (-)-(R,R)- and (+)-(S,S)-Muricatacin and Related Compounds
Tochtermann, Werner,Scholz, Gerhard,Bunte, Gudrun,Wolff, Christian,Peters, Eva-Maria,et al.
, p. 1069 - 1080 (2007/10/02)
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 98percent.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.Key Words: Lactones / (1S)-Camphanic acid / 2-Furanones / Dodecane diacid / Muricatacin / Annona muricata L.
