Synthesis of (卤)-Amathaspiramide F and Discovery of an Unusual Stereocontrolling Element for the [2,3]-Stevens Rearrangement

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• 作者：Arash Soheili ; Uttam K. Tambar
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：October 4, 2013
• 年：2013
• 卷：15
• 期：19
• 页码：5138-5141
• 全文大小：303K
• 年卷期：v.15,no.19(October 4, 2013)
• ISSN：1523-7052

文摘

A formal total synthesis of (卤)-amathaspiramide F through a tandem palladium-catalyzed allylic amination/[2,3]-Stevens rearrangement is reported. The unexpected diastereoselectivity of the [2,3]-Stevens rearrangement was controlled by the substitution patterns of an aromatic ring. This discovery represents a new stereocontrolling element for [2,3]-sigmatropic rearrangements in complex molecular settings.