Lithium Enolate with a Lithium-Alkyne Interaction in the Enantioselective Construction of Quaternary Carbon Centers: Concise Synthesis of (+)-Goniomitine
Yang Li
Department of Chemistry and Biochemistry, University of California, Santa Barbara, Santa Barbara, CA 93106 USA
Search for more papers by this authorElena Paola
Department of Chemistry and Biochemistry, University of California, Santa Barbara, Santa Barbara, CA 93106 USA
Search for more papers by this authorZongheng Wang
Department of Chemistry and Biochemistry, University of California, Santa Barbara, Santa Barbara, CA 93106 USA
Search for more papers by this authorProf. Dr. Gabriel Menard
Department of Chemistry and Biochemistry, University of California, Santa Barbara, Santa Barbara, CA 93106 USA
Search for more papers by this authorCorresponding Author
Prof. Dr. Armen Zakarian
Department of Chemistry and Biochemistry, University of California, Santa Barbara, Santa Barbara, CA 93106 USA
Center for Integrative Biology, Faculty of Sciences, Geroscience Center for Brain Health and Metabolism, Universidad Mayor, Santiago, Chile
Search for more papers by this authorYang Li
Department of Chemistry and Biochemistry, University of California, Santa Barbara, Santa Barbara, CA 93106 USA
Search for more papers by this authorElena Paola
Department of Chemistry and Biochemistry, University of California, Santa Barbara, Santa Barbara, CA 93106 USA
Search for more papers by this authorZongheng Wang
Department of Chemistry and Biochemistry, University of California, Santa Barbara, Santa Barbara, CA 93106 USA
Search for more papers by this authorProf. Dr. Gabriel Menard
Department of Chemistry and Biochemistry, University of California, Santa Barbara, Santa Barbara, CA 93106 USA
Search for more papers by this authorCorresponding Author
Prof. Dr. Armen Zakarian
Department of Chemistry and Biochemistry, University of California, Santa Barbara, Santa Barbara, CA 93106 USA
Center for Integrative Biology, Faculty of Sciences, Geroscience Center for Brain Health and Metabolism, Universidad Mayor, Santiago, Chile
Search for more papers by this authorAbstract
We report a method for direct enantioselective alkylation of 3-alkynoic and 2,3-alkendioic acids that form quaternary stereogenic centers, and application of this method to the total enantioselective synthesis of a complex alkaloid (+)-goniomitine. The methods were effective in the alkylation of both 3-alkynoic acids, 2,3-alkendioic acids substrates with a broad range of heterocyclic and functionalized alkyl group substituents. Accompanying crystallographic studies provide mechanistic insight into the structure of well-defined chiral aggregates, highlighting cation-π interactions between lithium and alkyne groups.
Conflict of interest
The authors declare no conflict of interest.
Open Research
Data Availability Statement
The data that support the findings of this study are available in the supplementary material of this article.
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