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

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• 作者：Julio Romero-Ibañez ; Leonardo Xochicale-Santana ; Leticia Quintero ; Lilia Fuentes ; Fernando Sartillo-Piscil
• 刊名：Journal of Natural Products
• 出版年：2016
• 出版时间：April 22, 2016
• 年：2016
• 卷：79
• 期：4
• 页码：1174-1178
• 全文大小：347K
• 年卷期：0
• ISSN：1520-6025

文摘

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.