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Additional recommended knowledge
This procedure was rediscovered and employed in the Holton Taxol total synthesis.
The methylene group in the reactant with adjacent carbonyl and acetyl substituents is acidic and can be deprotonated by strong non-nucleophilic bases such as lithium tetramethylpiperidide or lithium diisopropylamide (LDA) as in an aldol reaction. The thus formed enolate then gives a nucleophilic acyl substitution with the adjacent carbonyl of the acetyl group through a short lived intermediate oxirane. Acidic workup liberates the free hydroxyl group.
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Chan_rearrangement". A list of authors is available in Wikipedia.|