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- W2116789221 abstract "The total synthesis of plakortide E (1a) is reported. A novel palladium-catalyzed approach towards 1,2-dioxolanes as well as an alternative substrate-controlled route leading exclusively to cis-highly substituted 1,2-dioxolanes have been developed. A lipase-catalyzed kinetic resolution was employed to provide optically pure 1,2-dioxolane central cores. Coupling of the central cores and side chains was achieved by a modified Negishi reaction. All four isomeric structures of plakortide E methyl ester, namely, 26a-d were synthesized. One of the structures, 26d, was shown to be identical with the natural plakortide E methyl ester on the basis of (1)H, (13)C NMR spectra and specific rotation comparisons. With the plakortide E methyl ester (4S,6R,10R)-(-)-cis-26d and its other three isomers in hand, we successfully converted them into (3S,4S,6R,10R)-plakortone B (2a), and its isomers ent-2a, 2b and ent-2b via an intramolecular oxa-Michael addition/lactonization cascade reaction. Finally, saponification converted 1,2-dioxolane 26d into plakortide E (1a) whose absolute configuration (4S,6R,10R) was confirmed by comparison of spectral and physical data with those reported." @default.
- W2116789221 created "2016-06-24" @default.
- W2116789221 creator A5012035276 @default.
- W2116789221 creator A5025707880 @default.
- W2116789221 creator A5033146074 @default.
- W2116789221 creator A5052904581 @default.
- W2116789221 creator A5067319529 @default.
- W2116789221 date "2011-04-13" @default.
- W2116789221 modified "2023-08-10" @default.
- W2116789221 title "Total Synthesis of Plakortide E and Biomimetic Synthesis of Plakortone B" @default.
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- W2116789221 doi "https://doi.org/10.1002/chem.201003309" @default.
- W2116789221 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/21491517" @default.
- W2116789221 hasPublicationYear "2011" @default.