Recent insights into anatoxin‐<i>a</i>chemical synthesis, biomolecular targets, mechanisms of action and LC‐MS detection

An asymmetric total synthesis of [13C4]‐anatoxin‐a ([13C4]‐1) has been developed from commercially available ethyl [13C4]‐acetoacetate ([13C4]‐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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Concise Synthesis of (+)‐[¹³C₄]‐Anatoxin‐a by Dynamic Kinetic Resolution of a Cyclic Iminium Ion

Lacharity

Mailyan

Chen

et al. 2020

Angewandte Chemie

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Concise Synthesis of (+)‐[¹³C₄]‐Anatoxin‐a by Dynamic Kinetic Resolution of a Cyclic Iminium Ion

et al. 2020

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Recent insights into anatoxin‐achemical synthesis, biomolecular targets, mechanisms of action and LC‐MS detection

Cited by 2 publications

References 189 publications

Concise Synthesis of (+)‐[¹³C₄]‐Anatoxin‐a by Dynamic Kinetic Resolution of a Cyclic Iminium Ion

Concise Synthesis of (+)‐[¹³C₄]‐Anatoxin‐a by Dynamic Kinetic Resolution of a Cyclic Iminium Ion

Concise Synthesis of (+)‐[¹³C₄]‐Anatoxin‐a by Dynamic Kinetic Resolution of a Cyclic Iminium Ion

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Recent insights into anatoxin‐achemical synthesis, biomolecular targets, mechanisms of action and LC‐MS detection

Cited by 2 publications

References 189 publications

Concise Synthesis of (+)‐[13C4]‐Anatoxin‐a by Dynamic Kinetic Resolution of a Cyclic Iminium Ion

Concise Synthesis of (+)‐[13C4]‐Anatoxin‐a by Dynamic Kinetic Resolution of a Cyclic Iminium Ion

Concise Synthesis of (+)‐[13C4]‐Anatoxin‐a by Dynamic Kinetic Resolution of a Cyclic Iminium Ion

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Product

Resources

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Concise Synthesis of (+)‐[¹³C₄]‐Anatoxin‐a by Dynamic Kinetic Resolution of a Cyclic Iminium Ion

Concise Synthesis of (+)‐[¹³C₄]‐Anatoxin‐a by Dynamic Kinetic Resolution of a Cyclic Iminium Ion

Concise Synthesis of (+)‐[¹³C₄]‐Anatoxin‐a by Dynamic Kinetic Resolution of a Cyclic Iminium Ion