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 |
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Rok vydání: | 2016 |
Předmět: |
Lactams
Stereochemistry Pharmaceutical Science 010402 general chemistry 01 natural sciences Analytical Chemistry Tedanalactam Drug Discovery Piplaroxide Animals Organic chemistry Piperidones Pharmacology Molecular Structure biology Ants 010405 organic chemistry Chemistry Organic Chemistry Absolute configuration Total synthesis Stereoisomerism Atta cephalotes biology.organism_classification Amides 0104 chemical sciences Complementary and alternative medicine Insect Repellents Molecular Medicine Enantiomer Leafcutter ant |
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 |
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