A concise total synthesis of (R)-fluoxetine, a potent and selective serotonin reuptake inhibitor

Abstract

(R)-Fluoxetina, um inibidor potente e seletivo da recaptação da serotonina, foi sintetizada em seis etapas, 50% de rendimento total e 99% de excesso enantiomérico a partir do benzaldeído via alilação catalítica assimétrica empregando-se o sistema catalítico desenvolvido por Maruoka e colaboradores.(R)-Fluoxetine, potent and selective serotonin reuptake inhibitor, has been synthesized in six steps, 50% overall yield and 99% ee from benzaldehyde via catalytic asymmetric allylation with Maruoka´s catalyst.

Effects of treatment with fluoxetine on mandibular development: A morphological study in rats

“…Selective serotonin reuptake inhibitors (SSRI) are the class of drugs most used, with fluoxetine hydrochloride being widely prescribed (Jimenez-Solem et al, 2012), not only due to its efficacy, but also because of high tolerance to it (De Fátima et al, 2005). These medications selectively and potently block the serotonin transporters and receptors in the central nervous http://dx.doi.org/10.1016/j.acthis.2015.05.005 0065-1281/Published by Elsevier GmbH.…”

Efficient preparation of novel N-propargylic β-enaminones from the reaction of β-alkoxyvinyltrihalomethyl[carboxy]ketones and propargylamines

“…1-Methanesulfonate 2-propin-1-ol was synthesized as described in the literature. 22 We began our study by investigating the reaction of enone 1a with N-phenyl-N-prop-2-yn-1-amine 4 in equimolar amounts. For this purpose, we evaluated different alternative methodologies, including microwave irradiation, ultrasound irradiation and ionic liquids.…”

Enantioselective Allylation of Aldehydes Catalyzed by Diastereoisomeric Bis(tetrahydroisoquinoline) N,N′‐Dioxides

“…[3,4] Of numerous reactions, special attention is devoted to the enantioselective allylation of aldehydes, because it gives rise to chiral homoallyl alcohols that can serve as convenient building blocks for the synthesis of more complex compounds. [5] Typical examples include the syntheses of fluoxetine, [6] diospongine, [7] epicalyxin F, [8] rhoiptelol, [9] goniothalamin, [10] hyptolide, [11] fostriecine, [12] symbiodinolide, [13] and papulacandin D. [14] This resulted in the development of a series of organocatalysts having a chiral scaffold. These compounds could be roughly divided into three groups: (i) N,NЈ-dioxides with two pyridine moieties (most often bipyridines) possessing a stereogenic axis, (ii) N-oxides having the pyridine ring in-7040 96 %.…”