Synthesis of dizocilpine

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• 作者：Meng-Yang Chang ; ^{mychang@kmu.edu.tw} ; ^{mychang624@yahoo.com.tw} ; Yu-Ping Huang ; Tein-Wei Lee ; Yeh-Long Chen
• 关键词：Dizocilpine ; Dibenzosuberenone ; Aziridination ; Hydrogenolysis ; BF3· ; OEt2-promoted cyclization ; Desulfonylation
• 刊名：Tetrahedron
• 出版年：2012
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：22 April, 2012
• 卷：68
• 期：16
• 页码：3283-3287
• 文件大小：352 K

摘要

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路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.