Enantioselective Total Synthesis of the Neurotoxin Caramboxin

J Org Chem. 2024 May 3;89(9):6489-6493. doi: 10.1021/acs.joc.4c00541. Epub 2024 Apr 12.

Abstract

Herein, we report the first and efficient asymmetric total synthesis of the neurotoxin (-)-caramboxin. The key to success is the creation of a stereogenic center by using enantioselective catalytic phase-transfer α-alkylation of glycine imines, affording this unusual α-amino acid in good yields and up to 99% ee. This work validates the S configuration of the natural product.