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Concise Synthesis of (+)‐[ 13 C 4 ]‐Anatoxin‐a by Dynamic Kinetic Resolution of a Cyclic Iminium Ion
Author(s) -
Lacharity Jacob J.,
Mailyan Artur K.,
Chen Karen Y.,
Zakarian Armen
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202004464
Subject(s) - iminium , kinetic resolution , enantioselective synthesis , racemization , chemistry , kinetic isotope effect , kinetic energy , ion , resolution (logic) , organic synthesis , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , deuterium , computer science , physics , quantum mechanics , artificial intelligence
Abstract An asymmetric total synthesis of [ 13 C 4 ]‐anatoxin‐a ([ 13 C 4 ]‐ 1 ) has been developed from commercially available ethyl [ 13 C 4 ]‐acetoacetate ([ 13 C 4 ]‐ 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.