Journal of Organic Chemistry
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.
“This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see [insert ACS Articles on Request author-directed link to Published Work, see http://pubs.acs.org/doi/abs/10.1021/jo051691q
Shea, Kevin M.; Closser, Kristina D.; and Quintal, Miriam M., "Nicholas Reactions with Carboxylic Acids for the Synthesis of Macrocyclic Diolides" (2005). Chemistry: Faculty Publications, Smith College, Northampton, MA.