Synthesis of the Enantiomers of Tedanalactam and the First Total Synthesis and Configurational Assignment of (+)-Piplaroxide

Autor: Leonardo Xochicale-Santana, Julio Romero-Ibañez, Fernando Sartillo-Piscil, Leticia Quintero, Lilia Fuentes
Rok vydání: 2016
Předmět:
Zdroj: Journal of Natural Products. 79:1174-1178
ISSN: 1520-6025
0163-3864
DOI: 10.1021/acs.jnatprod.5b01041
Popis: Highlighting the recently established methodology for the direct synthesis of glycidic amides from tertiary allyl amines, the synthesis of the enantiomers of tedanalactam were completed in two steps from the corresponding chiral dihydropiperidine. Additionally, the (+)- and (-)-enantiomers of piplaroxide were obtained from their respective tedanalactam precursor, and the absolute configuration of the naturally occurring (+)-piplaroxide was determined. The present approach represents not only the shortest synthesis of (-)-tedanalactam but also the first total synthesis of (+)-piplaroxide, a repellent against the leafcutter ant Atta cephalotes.
Databáze: OpenAIRE