Document Type
Article
Publication Date
10-6-2005
Publication Title
Journal of Organic Chemistry
Abstract
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.
Volume
70
Issue
22
First Page
9088
Last Page
9091
Rights
“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
Version
Author's Accepted Manuscript
Recommended Citation
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.
https://scholarworks.smith.edu/chm_facpubs/9