Enantioselective synthesis of BMS-911278: a triple reuptake inhibitor

Autor:	Dawn Sun, Kristen N. Ryan, Daniel Smith, Subramaniam Krishnananthan, Min Hu, Dauh-Rurng Wu, Wenge Cui, Paul C. Lobben, Arvind Mathur, Shuang Liu, Jennifer Naginskaya, Richard E. Olson, Peng Li, Jianqing Li, Alicia Ng
Rok vydání:	2017
Předmět:	010405 organic chemistry Chemistry Stereochemistry Organic Chemistry Enantioselective synthesis Regioselectivity 010402 general chemistry 01 natural sciences Catalysis 0104 chemical sciences Inorganic Chemistry stomatognathic diseases Physical and Theoretical Chemistry Reuptake inhibitor
Zdroj:	Tetrahedron: Asymmetry. 28:196-202
ISSN:	0957-4166
Popis:	BMS-911278 was identified as a potent triple reuptake inhibitor potentially useful for the treatment of depression. The original racemic synthesis suffered from tedious and low recovery resolution and HPLC separation, as well as low-yielding hazardous N-demethylation at the API step. To support further preclinical studies, a scalable enantioselective synthesis was developed. Herein, we report an efficient asymmetric synthesis of BMS-911278 featuring two key steps: an enantioselective Miyaura reaction and an intramolecular regioselective cyclization.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::cd99d111ddccc082e4c2c89c67ec4c3f https://doi.org/10.1016/j.tetasy.2016.12.003 Zobrazit plný text záznamu Full Text from ScienceDirect