Stereoselective Synthesis of 2,8-Dioxabicyclo[3.3.1]nonane Derivatives via a Sequential Michael Addition/Bicyclization Reaction

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• 作者：Guodong Yin ; Tianbing Ren ; Yin Rao ; Yifan Zhou ; Zhexian Li ; Wenming Shu ; Anxin Wu
• 刊名：The Journal of Organic Chemistry
• 出版年：2013
• 出版时间：April 5, 2013
• 年：2013
• 卷：78
• 期：7
• 页码：3132-3141
• 全文大小：456K
• 年卷期：v.78,no.7(April 5, 2013)
• ISSN：1520-6904

文摘

A highly efficient and stereoselective synthesis of coumarin-, 1,3-cyclohexanedione-, and 1,4-naphthoquinone-fused 2,8-dioxabicyclo[3.3.1]nonanes is described. This was achieved via a sequential Michael addition/bicyclization reaction from easily accessible 3-(2-hydroxyphenyl)-1-phenylprop-2-en-1-one derivatives. Three chemical bonds (one C鈥揅 bond and two C鈥揙 bonds), two six-membered cycles, and two stereogenic centers were formed in a one-pot operation.