title: Synthesis of the Enantiomers of Tedanalactam and the First Total Synthesis and Configurational Assignment of (+)-Piplaroxide.
abstract: 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.
authors.affiliation: Centro de Investigación de la Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla (BUAP) , 14 Sur Esq. San Claudio, Colonia San Manuel, 72570 Puebla, México.
authors.forename: Julio
authors.initials: J
authors.lastname: Romero-Ibañez
authors.affiliation: Centro de Investigación de la Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla (BUAP) , 14 Sur Esq. San Claudio, Colonia San Manuel, 72570 Puebla, México.
authors.forename: Leonardo
authors.initials: L
authors.lastname: Xochicale-Santana
authors.affiliation: Centro de Investigación de la Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla (BUAP) , 14 Sur Esq. San Claudio, Colonia San Manuel, 72570 Puebla, México.
authors.forename: Leticia
authors.initials: L
authors.lastname: Quintero
authors.affiliation: Centro de Investigación de la Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla (BUAP) , 14 Sur Esq. San Claudio, Colonia San Manuel, 72570 Puebla, México.
authors.forename: Lilia
authors.initials: L
authors.lastname: Fuentes
authors.affiliation: Centro de Investigación de la Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla (BUAP) , 14 Sur Esq. San Claudio, Colonia San Manuel, 72570 Puebla, México.
authors.forename: Fernando
authors.initials: F
authors.lastname: Sartillo-Piscil
mesh_terms: D000577:Amides / Q000737:chemistry / Q000302:isolation & purification; D000818:Animals; D001000:Ants / Q000187:drug effects; D007302:Insect Repellents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010881:Piperidones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000577:Amides; D007302:Insect Repellents; D007769:Lactams; D010881:Piperidones; C000610616:piplaroxide; C552387:tedanalactam