title: Nicholas reactions with carboxylic acids for the synthesis of macrocyclic diolides.
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.
authors.affiliation: Department of Chemistry, Smith College, Northampton, Massachusetts 01063, USA. kshea@email.smith.edu
authors.forename: Kevin M
authors.initials: KM
authors.lastname: Shea
authors.forename: Kristina D
authors.initials: KD
authors.lastname: Closser
authors.forename: Miriam M
authors.initials: MM
authors.lastname: Quintal
mesh_terms: D002264:Carboxylic Acids / Q000737:chemistry*; D003500:Cyclization; D006859:Hydrogen / Q000737:chemistry; D007783:Lactones / Q000737:chemistry; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D002264:Carboxylic Acids; D007783:Lactones; D012717:Sesquiterpenes; D006859:Hydrogen