Title of article
Synthesis of dizocilpine
Author/Authors
Meng-Yang Chang، نويسنده , , Yuping Huang، نويسنده , , Tein-Wei Lee، نويسنده , , Yeh-Long Chen، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2012
Pages
5
From page
3283
To page
3287
Abstract
A simple five-step synthetic route toward dizocilpine (1) starting with dibenzosuberenone (2) in 28% of total yield is described. The facile route was carried from by aziridination of dibenzosuberenone (2) with NBS and chloramines-T in MeCN at reflux, hydrogenolysis of azridinyl ketone, Grignard methylation of amino ketone, BF3·OEt2-promoted cyclization of amino alcohol, and desulfonylation with Mg and Et3N in MeOH. Anthracene skeleton 9 is also synthesized via an intramolecular rearrangement of pinacol to pinacolone.
Keywords
Dizocilpine , aziridination , Dibenzosuberenone , Hydrogenolysis , BF3·OEt2-promoted cyclization , desulfonylation
Journal title
Tetrahedron
Serial Year
2012
Journal title
Tetrahedron
Record number
1104392
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