Nicholas Reactions with Carboxylic Acids for the Synthesis of Macrocyclic Diolides
The Journal of Organic Chemistry2005Vol. 70(22), pp. 9088–9091
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Abstract
[reaction: see text] We have developed a new strategy for the preparation of diolides using a cascade of Nicholas reactions. The carboxylic acid nucleophiles in these reactions are virtually unstudied participants in transformations of this type. Using this methodology, a 16-membered cobalt-complexed cyclic diyne is available in 28% yield over eight steps (an average of 85% per step). We can also easily access the uncomplexed diolide in one additional step.
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