Intramolecular Cyclobutadiene Cycloaddition/Cyclopropanation/Thermal Rearrangement: An Effective Strategy for the Asymmetric Syntheses of Pleocarpenene and Pleocarpenone

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• 作者：Michael J. Williams ; Holly L. Deak ; Marc L. Snapper
• 刊名：Journal of the American Chemical Society
• 出版年：2007
• 出版时间：January 24, 2007
• 年：2007
• 卷：129
• 期：3
• 页码：486 - 487
• 全文大小：58K
• 年卷期：v.129,no.3(January 24, 2007)
• ISSN：1520-5126

文摘

The first total synthesis of the guaiane sesquiterpene natural products pleocarpenone and pleocarpenene is described. An intramolecular cycloaddition of cyclobutadiene, followed by cyclopropanation and thermal fragmentation of the resulting highly strained intermediate, is the strategy used to achieve this synthesis. The asymmetric route allowed for confirmation of the absolute stereochemistry of these natural products.