Aza-Prins-Pinacol Approach to 7-Azabicyclo[2.2.1]heptanes: Syntheses of (±)-Epibatidine and (±)-Epiboxidine

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• 作者：Alan Armstrong ; Yunas Bhonoah ; Stephen E. Shanahan
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：October 12, 2007
• 年：2007
• 卷：72
• 期：21
• 页码：8019 - 8024
• 全文大小：134K
• 年卷期：v.72,no.21(October 12, 2007)
• ISSN：1520-6904

文摘

The syntheses of (±)-epibatidine and (±)-epiboxidine have been accomplished from commercial2-methoxy-3,4-dihydro-2H-pyran. A recently developed aza-Prins-pinacol rearrangement was employedfor the construction of the key 7-azabicyclo[2.2.1]heptane skeleton of these targets.