A Ring-Closing Metathesis-Based Approach to the Synthesis of (+)-Tetrabenazine

A modular stereoselective synthesis of the vesicular monoamine transport inhibitors (+)-tetrabenazine ((+)-1) and (+)-α-dihydrotetrabenazine ((+)-2) has been developed. The approach is based on amine 4 and acid 5 as the key building blocks, which were elaborated into macrolactam 3 by amide coupling...

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Bibliographic Details
Published inOrganic letters Vol. 14; no. 14; pp. 3752 - 3755
Main Authors Johannes, Manuel, Altmann, Karl-Heinz
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.07.2012
Amer Chemical Soc
Subjects
Amines - chemistry
Chemistry
Chemistry, Organic
Cyclization
Lactams, Macrocyclic - chemistry
Molecular Structure
Physical Sciences
Science & Technology
Stereoisomerism
Tetrabenazine - analogs & derivatives
Tetrabenazine - chemical synthesis
Tetrabenazine - chemistry
BENZOQUINOLIZINE DERIVATIVES
ABSOLUTE-CONFIGURATION
LIGANDS
VESICULAR MONOAMINE TRANSPORTER-2
TETRABENAZINE ENANTIOMERS
DIHYDROTETRABENAZINE
DRUGS
(+)-ALPHA-DIHYDROTETRABENAZINE
CYCLIZATION
CATALYSTS
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Summary:A modular stereoselective synthesis of the vesicular monoamine transport inhibitors (+)-tetrabenazine ((+)-1) and (+)-α-dihydrotetrabenazine ((+)-2) has been developed. The approach is based on amine 4 and acid 5 as the key building blocks, which were elaborated into macrolactam 3 by amide coupling and a subsequent highly E-selective RCM reaction. Macrolactam 3 could be converted into tetrabenazine in three known steps.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol301612q