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Updated: Dec 23, 2025
Synthesis and Structure Determination of µ-Conotoxin PIIIA Isomers with Different Disulfide Connectivities
Published on: October 2, 2018
Concise Synthesis of (+)-[13 C4 ]-Anatoxin-a by Dynamic Kinetic Resolution of a Cyclic Iminium Ion
Jacob J Lacharity1, Artur K Mailyan1, Karen Y Chen1
1Department of Chemistry and Biochemistry, University of California, Santa Barbara, CA, 93106-9510, USA.
Abstract:
An asymmetric total synthesis of [13 C4 ]-anatoxin-a ([13 C4 ]-1) has been developed from commercially available ethyl [13 C4 ]-acetoacetate ([13 C4 ]-15). The unique requirements associated with isotope incorporation inspired a new, robust, and highly scalable route, providing access to 0.110 g of this internal standard for use in the detection and precise quantification of anatoxin-a in freshwater. A highlight of the synthesis is a method that leverages a cyclic iminium ion racemization to achieve dynamic kinetic resolution in an enantioselective Morita-Baylis-Hillman (MBH) cyclization.
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