1431767-89-3Relevant academic research and scientific papers
Synthesis of the indoloazocine derivatives from a chiral indol amide-stabilized sulfur ylide
Juárez-Calderón, Maira,Aparicio, David M.,Gnecco, Dino,Juárez, Jorge R.,Orea, Laura,Mendoza, Angel,Sartillo-Piscil, Fernando,Del Olmo, Esther,Terán, Joel L.
, p. 2729 - 2732 (2013/06/26)
We present here a synthetic route for the access to a series of diverse indoloazocine derivatives through selective epoxidation of chiral sulfonium salt 4, which reacts with diverse aromatic and aliphatic aldehydes to give trans-glycidic amides, followed by an intramolecular electrophilic aromatic substitution promoted by Cu(OTf)2 giving the desired heterocyclic compound in a high chemical yield. Using this strategy, the total synthesis of (S,R)-(+)-norbalasubramide was achieved.
The use of sodium chlorite in the direct synthesis of glycidic amides: Enantiopure synthesis of both enantiomers of norbalasubramide
Fuentes, Lilia,Hernández-Juarez, Mireya,Terán, Joel L.,Quintero, Leticia,Sartillo-Piscil, Fernando
, p. 878 - 882 (2013/05/22)
Recently, the first direct method for preparing 2,3-epoxyamides (glycidic amides) was disclosed. Now in this letter, the enantiopure synthesis of both enantiomers of norbalasubramide featuring this synthetic method is reported. To this end, chiral N-allyltryptamine 12 was prepared and transformed into an inseparable mixture of diastereomeric epoxyamides 13a/13b, which were submitted to intramolecular cyclization with Cu(OTf)2 to afford a separable mixture of eight-membered ring lactams 14a and 14b. Finally, after removal of the protective group and the chiral auxiliary an enantiopure synthesis of the title compounds was completed. Georg Thieme Verlag Stuttgart · New York.
