Synthesis of Dibenzo[b,d]pyran-6-ones Based on [3 + 3] Cyclizations of 1,3-Bis(silyl enol ethers) with 3-Silyloxy-2-en-1-ones

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• 作者：Ibrar Hussain ; Van Thi Hong Nguyen ; Mirza Arfan Yawer ; Tuan Thanh Dang ; Christine Fischer ; Helmut Reinke ; Peter Langer
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：August 3, 2007
• 年：2007
• 卷：72
• 期：16
• 页码：6255 - 6258
• 全文大小：89K
• 年卷期：v.72,no.16(August 3, 2007)
• ISSN：1520-6904

文摘

LE>left" HSPACE=5>Functionalized dibenzo[b,d]pyran-6-ones were prepared byformal [3 + 3] cyclization of 1,3-bis(silyl enol ethers) with3-silyloxy-2-en-1-ones or 1,1-diacetylcyclopropane to givefunctionalized salicylates, Suzuki cross-coupling reactionsof the corresponding triflates, and subsequent BBr₃-mediatedlactonization. A second approach to dibenzo[b,d]pyran-6-ones relies on the [3 + 3] cyclization of 1,3-bis(silyl enolethers) with 1-(2-methoxyphenyl)-1-(trimethylsilyloxy)alk-1-en-3-ones and subsequent BBr₃-mediated lactonization.