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Enantiodivergent Synthesis of Benzoquinolizidinones from L-Glutamic Acid

Benzoquinolizidinone systems were synthesized in both enantiomeric forms from L-glutamic acid. The key chiral arylethylglutarimide intermediate was synthesized from dibenzylamino-glutamate and homoveratrylamine. Aldol reaction of the glutarimide afforded a mixture of syn and anti-aldol adducts. Subs...

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Detalles Bibliográficos
Autores principales: Kuntiyong, Punlop, Namborisut, Duangkamon, Phakdeeyothin, Kunita, Chatpreecha, Rungrawin, Thammapichai, Kittisak
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8512815/
https://www.ncbi.nlm.nih.gov/pubmed/34641410
http://dx.doi.org/10.3390/molecules26195866
Descripción
Sumario:Benzoquinolizidinone systems were synthesized in both enantiomeric forms from L-glutamic acid. The key chiral arylethylglutarimide intermediate was synthesized from dibenzylamino-glutamate and homoveratrylamine. Aldol reaction of the glutarimide afforded a mixture of syn and anti-aldol adducts. Subsequent regioselective hydride reduction of the glutarimide carbonyl followed by N-acyliminium ion cyclization afforded a product with opposite absolute configurations at C3 and C11b. Cope elimination of the dibenzylamino group then converted the two diastereomers into enantiomers.