A highly enantioselective synthetic method towards the α2c-adrenoceptor antagonist ORM-10921

文献情報

出版日 2019-01-30

DOI 10.1039/C8QO01166D

インパクトファクター 5.281

著者

Qiaoning Ma, Xiaodi Yang, Xinsheng Lei

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要旨

The preparation of ORM-10921, a selective α2C-adrenoceptor antagonist with promising anti-psychotic properties, was successfully achieved using asymmetric α-alkylation of α,β-unsaturated imide and Bischler–Napieralski cyclization/asymmetric reduction as the key steps. When the tetracyclic iminium 11S was used in the reduction, the diastereo-selectivity was poor, from which four stereoisomers of ORM-10921 were obtained, respectively. However, the diastereoselectivity could be significantly improved (with dr up to >97 : 3) when the tricyclic imine substrate 19S was applied in this reduction, suggesting an additional chelation from the side-chain methoxy group in the transition state. According to this protocol, ORM-10921 was accomplished in a highly enantioselective manner. In addition, two analogs 26Aa and 26Ba were prepared using this novel method, and the absolute configurations were unambiguously assigned by single crystal X-ray crystallography.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

A highly enantioselective synthetic method towards the α2c-adrenoceptor antagonist ORM-10921

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