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Author Notes:
Correspondence: Albert Padwa; Tel.: +404 727 0283; Fax: +404 727 6629; Email: chemap@emory.edu
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Research Funding:
We appreciate the financial support provided by the National Institutes of Health (GM 059384) and the National Science Foundation (CHE-0450779).
Lewis acid-promoted α-hydroxy β-dicarbonyl to α-ketol ester rearrangement
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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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© 2006 Elsevier Ltd. All rights reserved.
This is an Open Access work distributed under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs 2.5 Generic License (http://creativecommons.org/licenses/by-nc-nd/2.5/).
