An improved asymmetric synthetic route to a novel triple uptake inhibitor antidepressant (2S,4R,5R)-2-benzhydryl-5-((4-methoxybenzyl)amino)-tetrahydro-2H-pyran-4 -ol (D-142)

作者：Gopishetty Bhaskar; Gogoi Sanjib; Dutta Aloke K^*

来源：Tetrahedron: Asymmetry , 2011, 22(10): 1081-1086.

DOI：10.1016/j.tetasy.2011.05.012

Triple monoamine reuptake inhibitors have been implicated in the development of a new generation of antidepressants with higher efficacy than the currently existing therapies. In this paper, we have developed an alternative efficient synthetic route for triple monoamine reuptake inhibitor D-142 in 18.5% overall yield in 11 steps starting from diphenylmethane. D-142 was developed by us recently. The key step of the present synthetic strategy is the preferential formation of a bromohydrin from olefin via a cis-bromonium intermediate, which introduced significant efficiency in the overall synthesis. Furthermore, we have developed an efficient way to recycle the optically active intermediate diol back to the desired chiral epoxide.

• 出版日期2011-5-31