A Facile, Expeditious Route to the Benzooxabicyclo [3.2. 1] octane System. Application to a Short, High-Yield Synthesis of Filiformin

A Nath, J Mal, RV Venkateswaran

文献索引：Nath, Asok; Mal, Jayati; Venkateswaran, Ramanathapuram V. Journal of Organic Chemistry, 1996 , vol. 61, # 13 p. 4391 - 4394

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被引用次数: 23

摘要

A facile and efficacious route to the benzooxabicyclo [3.2. 1] octane system has been developed and applied to a synthesis of filiformin (1). The cycloaddition of ethylene to the methoxychromone 13 furnished the oxetanol 14 through a tandem cycloaddition and γ- hydrogen abstraction sequence. Lithium aluminum hydride reduction to the diol 15 followed by acid-catalyzed rearrangement produced benzooxabicyclooctanone (16), arising from ...