title: 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).
abstract: 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-bromoinum 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.
authors.affiliation: Wayne State University, Department of Pharmaceutical Sciences, Detroit, MI 48202, USA.
authors.forename: Bhaskar
authors.initials: B
authors.lastname: Gopishetty
authors.forename: Sanjib
authors.initials: S
authors.lastname: Gogoi
authors.forename: Aloke
authors.initials: A
authors.lastname: Dutta