Toward the Synthesis of Phomoidride D

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• 作者：Graham K. Murphy ; Tatsuya Shirahata ; Naoto Hama ; Aaron Bedermann ; Ping Dong ; Travis C. McMahon ; Barry M. Twenter ; David A. Spiegel ; Ivar M. McDonald ; Nobuaki Taniguchi ; Munenori Inoue ; John L. Wood
• 刊名：The Journal of Organic Chemistry
• 出版年：2013
• 出版时间：January 18, 2013
• 年：2013
• 卷：78
• 期：2
• 页码：477-489
• 全文大小：670K
• 年卷期：v.78,no.2(January 18, 2013)
• ISSN：1520-6904

文摘

An efficient and highly stereoselective approach toward the phomoidride family of natural products is described. The carbocyclic core structure was assembled using a tandem phenolic oxidation/Diels鈥揂lder cycloaddition and a tandem 5-exo-trig/5-exo-trig radical cyclization to deliver an isotwistane intermediate that, upon a late-stage xanthate-initiated Grob fragmentation, furnishes the requisite bicyclo[4.3.1]decene.