Tetrahedron letters

Lewis acid-promoted α-hydroxy β-dicarbonyl to α-ketol ester rearrangement

X Hong, JM Mejía-Oneto, A Padwa

文献索引：Hong, Xuechuan; Mejia-Oneto, Jose M.; Padwa, Albert Tetrahedron Letters, 2006 , vol. 47, # 47 p. 8387 - 8390

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被引用次数: 12

摘要

The decarbomethoxylation reaction of a substituted α-hydroxy-α-carbomethoxy pentacyclic substituted ketone, used as an advanced intermediate in the synthesis of the alkaloid aspidophytine, can be effected by heating with MgI2 in CH3CN. The reaction was shown to proceed by a novel α-hydroxy β-dicarbonyl to α-ketol ester rearrangement. It was possible to isolate a carbonate intermediate in 75% yield, thereby providing support for the proposed ...