Stereoselective Total Synthesis of Vilanterol

Abstract

A total synthesis of Vilanterol, a potent molecule for asthma and chronic obstructive pulmonary
disease and a long-acting β2-adrenoceptor agonist, is carried out effectively using a multistep manner.
A key intermediate tert-butyl-(R)- dimethyl benzo dioxin 2-hydroxy ethyl carbamate 8 was synthesized
using C1- Wittig on aromatic aldehyde, Sharpless asymmetric dihydroxylation, selective tosyl
protection of primary alcohol. Additionally, another key intermediate 9 was synthesized using alcohol
and dibromo hexane compound via substitution reactions. Combining of the two synthetic fragments to
create an acceptable amount of Vilanterol.