ISSN:
0170-2041
Keywords:
Lactones
;
(1S)-Camphanic acid
;
2-Furanones
;
Dodecane diacid
;
Muricatacin
;
Annona muricata L.
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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 CompoundsThe 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.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1992199201176
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