Synthesis of the indoloazocine derivatives from a chiral indol amide-stabilized sulfur ylide

Autor:	Joel L. Terán, Esther del Olmo, Dino Gnecco, Fernando Sartillo-Piscil, Maira Juarez‐Calderon, Laura Orea, Angel Mendoza, David M. Aparicio, Jorge R. Juárez
Rok vydání:	2013
Předmět:	chemistry.chemical_classification Sulfonium Organic Chemistry Total synthesis Electrophilic aromatic substitution Biochemistry Medicinal chemistry chemistry.chemical_compound chemistry Heterocyclic compound Ylide Intramolecular force Yield (chemistry) Amide Drug Discovery
Zdroj:	Tetrahedron Letters. 54:2729-2732
ISSN:	0040-4039
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::e3cba56de2229253f5acfd8256f6f6b3 https://doi.org/10.1016/j.tetlet.2013.03.068 Zobrazit plný text záznamu Full Text from ScienceDirect