Chemistry of trans-Resveratrol with Singlet Oxygen: [2 + 2] Addition, [4 + 2] Addition, and Formation of the Phytoalexin Moracin M

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• 作者：Jeff A. Celaje ; Dong Zhang ; Angela M. Guerrero ; Matthias Selke
• 刊名：Organic Letters
• 出版年：2011
• 出版时间：September 16, 2011
• 年：2011
• 卷：13
• 期：18
• 页码：4846-4849
• 全文大小：699K
• 年卷期：v.13,no.18(September 16, 2011)
• ISSN：1523-7052

文摘

Resveratrol (1) reacts with singlet oxygen by two major pathways: A [2 + 2] cycloaddition forming a transient dioxetane that cleaves into the corresponding aldehydes and a [4 + 2] cycloaddition forming an endoperoxide that, upon heating, undergoes a rearrangement to moracin M. The rate constant by which singlet oxygen is removed by 1 (k_T) was determined by time-resolved infrared luminescence spectroscopy to be 1.5 脳 10⁶ M^鈥?鈥塻ec^鈥? in CD₃OD, smaller than previously reported values. Chemical reaction accounts for ca. 25% of k_T.