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The enantioselective synthesis of marmelo oxide a and marmelo oxide b and the assignment of the absolute configurations of marmelo oxides


, : The enantioselective synthesis of marmelo oxide a and marmelo oxide b and the assignment of the absolute configurations of marmelo oxides. Agricultural & Biological Chemistry 48(5): 1217-1222

(+)-Marmelo oxide A and (-)-marmelo oxide B were stereoselectively synthesized from D-glutamic acid via (-)-marmelo lactones A and B. The absolute configurations of marmleo oxides were determined to be the (+)-oxide A having the (2R, 4R) and (+)-oxide B having (2S, 4R) configurations.


Accession: 006670981

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Related references

Nishida, Y.F.kushima, Y.O.rui, H.M.guro, H., 1984: The enantioselective synthesis of marmelo oxides A and B and the assignment of the absolute configurations of marmelo oxides. Agricultural and biological chemistry 48(5): 1217-1221

Nishida Y.; Ohrui H.; Meguro H., 1984: The synthesis of dextro marmelo lactones a and b and the assignment of the absolute configurations of marmelo lactones. (+)-Marmelo lactones A (VA) and B (VB) were synthesized from erythro-.gamma.-methyl-L-glutamic acid (IA) and threo acid (IB), respectively. The absolute configurations of natural marmelo lactones were determined to be (2R, 4S) for (+)-marmelo lact...

Nishida, Y.O.rui, H.M.guro, H., 1984: The synthesis of (+)-marmelo lactones A and B and the assignment of the absolute configurations of marmelo lactones. Agricultural and biological chemistry 48(5): 1211-1216

Nishida, Y.O.rui, H.M.guro, H., 1983: Absolute configurations of marmelo oxides. Agricultural and biological chemistry 47(12): 2969-2971

Naf R.; Velluz A., 1991: Isolation of acyclic precursors of the marmelo oxides the marmelo lactones and the quince oxepine from quince fruit cydonia oblonga mil. (2E,4E)-2,7-Dimethyloctadiene-1,8-diol (5), (2E,4E,7Z)-2,7-dimethyldecatriene-1,10-diol (6) and (4E,6E)-2,7-dimethyl-8-hydroxyoctadienoic acid (7), three acyclic precursors of the marmelo oxides (1), of the marmelo lactones (2) and of quince oxepi...

Ishihara, M.; Tsuneya, T.; Shiota, H.; Shiga, M.; Yokoyama, Y., 1983: The absolute configurations of marmelo lactones. Elucidation of the absolute configurations of two previously identified monoterpenic gamma -lactones from the essential oil of quince fruit is based on chiroptical data.

Srikrishna A.; Krishnan K., 1989: Synthesis of racemic marmelo oxides by a radical cyclization reaction. Journal of Organic Chemistry 54(16): 3981-3983

Nishida, Y.; Ohrui, H.; Meguro, H., 1983: Synthesis of(+)-marmelo lactone A and (+)-marmelo lactone B. Synthesis of the two lactones previously identified in the essential oil of quince fruit was used to establish further their absolute configurations.

Kitahara, T.S.imizu, H., 1998: Synthesis of a glycosidic precursor of isomeric marmelo oxides, volatile components of quince fruit, Cydonia oblonga. Journal of natural products 61(4): 551-554

Nishida Y.; Ohrui H.; Meguro H., 1983: Synthesis of dextro marmelo lactone a and dextro marmelo lactone b. Agricultural & Biological Chemistry 47(9): 2123-2126