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

Authors
  • Xuechuan Hong
  • José M. Mejía-Oneto
  • Albert Padwa
Publication Date
Nov 20, 2006
Source
PMC
Keywords
License
Unknown

Abstract

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 elected 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 pathway.

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