First Total Syntheses of Beauvericin A and allo-Beauvericin A

Natsumi Kozakai; Seiya Endo; Atsushi Nakayama; Riku Horinouchi; Makoto Yoshida; Masayoshi Arai; Tetsuro Shinada

doi:10.1021/acsomega.4c00278

First Total Syntheses of Beauvericin A and allo-Beauvericin A

ACS Omega. 2024 Feb 26;9(10):12228-12236. doi: 10.1021/acsomega.4c00278. eCollection 2024 Mar 12.

Authors

Natsumi Kozakai¹, Seiya Endo¹, Atsushi Nakayama¹, Riku Horinouchi², Makoto Yoshida², Masayoshi Arai², Tetsuro Shinada¹

Affiliations

¹ Graduate School of Science, Osaka Metropolitan University, 3-3-138 Sugimoto, Sumiyoshi, Osaka 558-8585, Japan.
² Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita , Osaka 565-0871, Japan.

Abstract

The first total syntheses of beauvericin A and allo-beauvericin A were achieved. N-Methyl-l-phenylalanine, (2R)-hydroxylvaleric acid, and (2R,3S)- or (2R,3R)-2-hydroxy-2-methylpentanoic acid were linked and cyclized to form the target natural products. The structure of synthetic beauvericin A was confirmed by X-ray crystallographic analysis. NMR data of the synthetic beauvericins were identical with those of the reported natural products. These results secure the structures of natural products, as originally proposed in the isolation studies.